4-Tributylstannyl-3,6-dihydro-2H-pyran → [2-(3,6-Dihydro-2H-pyran-4-yl)-5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl]-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

HRID 1931023Notes

Reaction equation

HRID 1931023 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[CH2:36][CH2:37][O:38][CH2:39][CH:40]=1)CCC>>[O:38]1[CH2:37][CH:36]=[C:35]([C:2]2[N:7]=[C:6]3[CH2:8][N:9]([C:11]([C:13]4[CH:18]=[C:17]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:16]=[CH:15][C:14]=4[O:23][C@@H:24]([CH3:29])[C:25]([F:28])([F:26])[F:27])=[O:12])[CH2:10][C:5]3=[CH:4][CH:3]=2)[CH2:40][CH2:39]1

Participants

3

Reactant 2

HCID 222522584-Tributylstannyl-3,6-dihydro-2H-pyranHCID 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 57753251[2-(3,6-Dihydro-2H-pyran-4-yl)-5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl]-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-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-(3,6-dihydro-2H-pyran-4-yl)-stannane. White solid. MS (m/e): 497.4 [M+H]+, 100%).

Sources & evidence

ORD record
ord-944ea8d7769a4dcdb1fe625c1e37eec9
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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