Tributyl(3-(trifluoromethyl)phenyl)stannane → (5-Methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[2-(3-trifluoromethyl-phenyl)-5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl]-methanone

HRID 225749Notes

Reaction equation

HRID 225749 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH2:8][N:9]([C:11]([C:13]3[CH:18]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=3[O:23][C@@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])=[O:12])[CH2:10][C:5]2=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=1)CCC>>[CH3:22][S:19]([C:17]1[CH:16]=[CH:15][C:14]([O:23][C@@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])=[C:13]([C:11]([N:9]2[CH2:10][C:5]3[C:6](=[N:7][C:2]([C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=4)=[CH:3][CH:4]=3)[CH2:8]2)=[O:12])[CH:18]=1)(=[O:21])=[O:20]

Participants

3

Reactant 2

HCID 2777910Tributyl(3-(trifluoromethyl)phenyl)stannaneHCID 57753234(2-Chloro-5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

Product 1

HCID 57753583(5-Methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[2-(3-trifluoromethyl-phenyl)-5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl]-methanone

Procedure

Prepared in analogy to Example A54(a) from (2-chloro-5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone (Example C4) and tributyl-[3-(trifluoromethyl)phenyl]-stannane. White solid. MS (m/e): 559.2 [M+H]+, 100%).

Sources & evidence

ORD record
ord-6cfcee26a36643f58dd3e8f4abc443be
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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