Reaktion #474680

Reaktionsgleichung

7

tert-Butyl 2-(benzo[d]furan-2-ylcarbonylamino)-4-[(trifluoromethyl)sulfonyloxy]-thiophene-3-carboxylate

NaHCO3

1,2-dimethoxyethane

→

Compound 40

Ausbeute 48.0%

2-(benzo[d]furan-2-ylcarbonylamino)-4-benzothiazol-5-ylthiophene-3-carboxylic acid

Ausbeute 48.0%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe suspension was bubbled with argon for 5 min
2. 2
   FiltrationThe solid was filtered off
3. 3
   Extraktionthe filtrate was extracted with EtOAc (10 ml×2)
4. 4
   TrocknenThe combined organic layers were dried (Na2SO4)
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe compound 39 was purified by HPLC
7. 7
   workup.DISSOLUTIONThe 39 was dissolved in CH2Cl2 (2 ml)
8. 8
   workup.ADDITIONTFA (0.5 ml) was added
9. 9
   SonstigeThe solvent was removed in vacuo
10. 10
    workup.ADDITIONThe residue was treated with MeOH (2 mL)
11. 11
    Sonstigethe solid was collected by centrifuge
12. 12
    Waschenwashed with MeOH

Vorschrift

To a solution of 7 (49 mg, 0.1 mmol) in 1,2-dimethoxyethane (DME, 2 mL) and EtOH (1 mL) was added 37 (31 mg, 0.12 mmol), 0.5 M NaHCO3 (1 mL). The suspension was bubbled with argon for 5 min before adding Pd(PPh3) (38, 12 mg, 0.01 mmol). The reaction mixture was heated at 110° C. for 30 min using microwave initiator. The solid was filtered off and the filtrate was extracted with EtOAc (10 ml×2). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The compound 39 was purified by HPLC. The 39 was dissolved in CH2Cl2 (2 ml) and TFA (0.5 ml) was added. The mixture was stirred for 2 h at r.t. The solvent was removed in vacuo. The residue was treated with MeOH (2 mL) and the solid was collected by centrifuge and washed with MeOH. Compound 40 (20 mg, 48%) was obtained as yellow solid. LC-MS: calcd. for C21H12N2O4S2: 419 (M−1).

Quelle