Benzyl (2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate → {4-[5-Amino-2-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-2-chloro-phenyl}-carbamic acid benzyl ester

HRID 1958185Notes

Reaction equation

HRID 1958185 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:14])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[C:15]1([CH2:21][O:22][C:23](=[O:41])[NH:24][C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:26]=2[Cl:40])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:21]([O:22][C:23](=[O:41])[NH:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[N:6][CH:5]=[C:4]([NH2:14])[CH:3]=2)=[CH:27][C:26]=1[Cl:40])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 46739621Benzyl (2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 672810445-Bromo-6-(2,2,2-trifluoroethoxy)-pyridin-3-ylamine

Product 1

HCID 67280667{4-[5-Amino-2-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-2-chloro-phenyl}-carbamic acid benzyl ester

Procedure

The title compound was synthesized in analogy to Example E, using 5-bromo-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine (example C) and N-[2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-carbamic acid phenylmethyl ester (CAN 1218791-42-4) as starting materials; MS (EI) 452.1 (M+H)+.

Sources & evidence

ORD record
ord-937d1ed5c2544a4498b82998792f1c75
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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