Reaktion #624383

Reaktionsgleichung

1-chloroisoquinoline-7-carboxylic acid

RuPhos

BrettPhos

sodium tert-butoxide

lithium bistrimethylsilylamide

t-butylamine

→

1-(tert-butylamino)isoquinoline-7-carboxylic acid

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vessel was sealed
2. 2
   TemperaturThe reaction was cooled down to room temperature
3. 3
   TemperaturThe reaction mixture was heated to 110° C.
4. 4
   workup.WAITleft
5. 5
   workup.STIRRINGstirring overnight
6. 6
   TemperaturThe reaction mixture was cooled down to room temperature
7. 7
   Filtrationfiltered through celite
8. 8
   Waschenrinsed with methanol
9. 9
   EinengenThe filtrate was concentrated under reduced pressure and 1N aqueous sodium hydroxide (1 mL)
10. 10
    workup.ADDITIONwas added
11. 11
    SonstigePartitioned between ethyl acetate
12. 12
    workup.ADDITIONa mixture of water and 1N aqueous sodium hydroxide
13. 13
    SonstigeThe layers were separated
14. 14
    ExtraktionThe aqueous layer was extracted into ethyl acetate
15. 15
    TrocknenThe extracts were dried over magnesium sulfate
16. 16
    Filtrationfiltered
17. 17
    Einengenconcentrated under reduced pressure

Vorschrift

To a suspension of 1-chloroisoquinoline-7-carboxylic acid (100 mg, 0.482 mmol), RuPhos (6.5 mg, 0.014 mmol), BrettPhos (11.2 mg, 0.014 mmol) and sodium tert-butoxide (70.2 mg, 0.723 mmol) in dioxane (0.5 mL) was added t-butylamine (0.254 mL, 2.41 mmol). The vessel was sealed and mixture was heated to 110° C. and stirred overnight. The reaction was cooled down to room temperature and lithium bistrimethylsilylamide (0.136 mL, 0.723 mmol) was added. The reaction mixture was heated to 110° C. and left stirring overnight. The reaction mixture was cooled down to room temperature and filtered through celite and rinsed with methanol. The filtrate was concentrated under reduced pressure and 1N aqueous sodium hydroxide (1 mL) was added. Partitioned between ethyl acetate and a mixture of water and 1N aqueous sodium hydroxide. The layers were separated and the aqueous layer was acidified to pH 4. The aqueous layer was extracted into ethyl acetate. The extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain 1-(tert-butylamino)isoquinoline-7-carboxylic acid.

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