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

HRID 1924768Notes

Reaction equation

HRID 1924768 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:34]=[N:35][NH:36][CH:37]=2)O1>>[NH:35]1[CH:34]=[C:33]([C:2]2[N:7]=[C:6]3[S:8][C:9]([NH:11][C:12](=[O:24])[C:13]4[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[CH:15][CH:14]=4)=[N:10][C:5]3=[CH:4][CH:3]=2)[CH:37]=[N:36]1

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Product 1

HCID 44549076N-(5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamideYield 37%

Procedure

The titled compound (yield=37%) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 2F (Example 2) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 3.48 (s, 3H) 7.57 (d, J=8.34 Hz, 2H) 7.83 (d, J=8.59 Hz, 1H) 8.02-8.17 (m, 3H) 8.28 (s, 2H) 12.88 (s, 1H); ESI-MS: m/z 394.0 (M+H)+.

Sources & evidence

ORD record
ord-f628e525189747309779d8749bdf7afa
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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