4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 4-(1-hydroxy-2-methylpropan-2-yl)-N-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamide

HRID 1924784Notes

Reaction equation

HRID 1924784 reaction equation
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:24])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)O1>>[OH:21][CH2:20][C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]([NH:11][C:9]2[S:8][C:6]3[C:5]([N:10]=2)=[CH:4][CH:3]=[C:2]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[N:7]=3)=[O:24])=[CH:14][CH:15]=1)([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Product 1

HCID 445486194-(1-hydroxy-2-methylpropan-2-yl)-N-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamideYield 63%

Procedure

The titled compound (yield=63%, white solid) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except 2F (Example 2) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (s, 6H) 3.49 (s, 2H) 7.59 (d, J=8.59 Hz, 2H) 8.10-8.12 (d, J=8.59 Hz, 2H) 8.31-8.36 (m, 1H) 8.37-8.44 (m, 3H) 8.85 (d, J=5.31 Hz, 2H) 13.15 (s, 1H); ESI-MS: m/z 405.0 (M+H)+.

Sources & evidence

ORD record
ord-bc344cce975e4126a5949024c7c3cc34
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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