2-(Tributylstannyl)-1,3-thiazole → (2E)-N-Indol-5-yl-3-[2-(I,3-thiazol-2-yl)-4-(trifluoromethyl)phenyl]prop-2-enamide

HRID 730293Notes

Reaction equation

HRID 730293 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=[O:15].C([Sn](CCCC)(CCCC)[C:31]1[S:32][CH:33]=[CH:34][N:35]=1)CCC>>[NH:22]1[C:23]2[C:19](=[CH:18][C:17]([NH:16][C:14](=[O:15])/[CH:13]=[CH:12]/[C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=3[C:31]3[S:32][CH:33]=[CH:34][N:35]=3)=[CH:25][CH:24]=2)[CH:20]=[CH:21]1

Participants

3

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 57807978(2E)-3-[2-Bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide

Product 1

HCID 57807981(2E)-N-Indol-5-yl-3-[2-(I,3-thiazol-2-yl)-4-(trifluoromethyl)phenyl]prop-2-enamide

Procedure

Analogous to the procedure used to prepare Example 100, (2E)-3-[2-bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide, Example 97, (100 mg, 0.24 mmol) and 2-tributylstannylthiazole (155 mg, 0.42 mmol, Frontier Scientific) provided, after purification by silica gel chromatography (gradient: 0-35%EtOAc in hexane), the title product as an orange solid. MP 203-204° C. MS (ESI, pos. ion) m/z: 414 (M+1).

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography (gradient: 0-35%EtOAc in hexane)

Sources & evidence

ORD record
ord-7dd21044a5e1404abb3e4af8f29ec485
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

Loading…