반응 #1748543

반응 방정식

2-stannylindole

triphenylphosphine

LiCl

2-bromopropene

→

2-(2-propenyl)indole

용매

DMF

반응 조건

후처리

1. 1
   기타the suspension degassed
2. 2
   기타by bubbling Ar for 20 min
3. 3
   기타after degassing for an additional 10 min
4. 4
   workup.ADDITIONThe suspension was then diluted with TBME (100 mL)
5. 5
   세척washed with brine (2×25 mL)
6. 6
   건조The extract was dried (MgSO4)
7. 7
   농축concentrated under reduced pressure
8. 8
   기타to give a residue that
9. 9
   기타was purified by flash chromatography

실험 절차

The 2-stannylindole 23-1 (1.280 g, 2.34 mmol; prepared using methods described in WO 03/010141), triphenylphosphine (0.065 g, 0.25 mmol), Cul (0.045 g, 0.24 mmol), LiCl (0.200 g, 4.72 mmol) and 2-bromopropene (0.444 mL, 5.00 mmol) were dissolved in DMF (6 mL) and the suspension degassed by bubbling Ar for 20 min. Pd2(dba)3 (0.035 g, 0.034 mmol) was added and after degassing for an additional 10 min, the reaction mixture was heated to 100° C. overnight. The suspension was then diluted with TBME (100 mL) and washed with brine (2×25 mL). The extract was dried (MgSO4) and concentrated under reduced pressure to give a residue that was purified by flash chromatography using 5-10% EtOAc in hexane as eluent. The desired 2-(2-propenyl)indole 23-2 was obtained as beige solid (0.57 g, 81% yield): MS-ES m/z 298.1 (MH+). The methyl ester 23-2 was saponified in the usual way (NaOH/DMSO) to give the corresponding carboxylic acid 23-3 in 96% yield: MS-ES m/z 284.1 (MH+).

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