5-Bromo-3-((2-chloro-3,6-difluorobenzyl)oxy)pyridin-2-amine → HCID 58885829, compound

HRID 1627531Notes

Reaction equation

HRID 1627531 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=2[Cl:19])[C:5]([NH2:8])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][C:31]([NH:34][S:35]([CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])(=[O:37])=[O:36])=[CH:30][CH:29]=2)O1>>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][S:35]([CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])(=[O:36])=[O:37])=[CH:30][CH:29]=2)=[CH:3][C:4]=1[O:9][CH2:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=1[Cl:19]

Participants

3

Reactant 2

HCID 211114915-Bromo-3-((2-chloro-3,6-difluorobenzyl)oxy)pyridin-2-amineHCID 588860212-(Diethylamino)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamide

Product 1

HCID 58885829HCID 58885829, compoundYield 60%

Procedure

2-diethylamino-ethanesulfonic acid {4-[6-amino-5-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-3-yl]-phenyl}-amide was prepared following the general Suzuki coupling procedure 3 from 5-bromo-3-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-2-ylamine and 2-diethylamino-ethanesulfonic acid [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide prepared in part 2 as a white solid in 60% yield.

Sources & evidence

ORD record
ord-8780a909bc3849a7b546c89a3eb8108f
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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