3,5-Dimethylpyrazole-4-boronic acid, pinacol ester → N-(5-(3,5-dimethyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide

HRID 1924769Notes

Reaction equation

HRID 1924769 reaction equation
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:23])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:24][C:25]1[C:29](B2OC(C)(C)C(C)(C)O2)=[C:28]([CH3:39])[NH:27][N:26]=1>>[CH3:24][C:25]1[C:29]([C:2]2[N:7]=[C:6]3[S:8][C:9]([NH:11][C:12](=[O:23])[C:13]4[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=4)=[N:10][C:5]3=[CH:4][CH:3]=2)=[C:28]([CH3:39])[NH:27][N:26]=1

Participants

3

Reactant 2

HCID 162177133,5-Dimethylpyrazole-4-boronic acid, pinacol esterHCID 58015365N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide

Product 1

HCID 44549075N-(5-(3,5-dimethyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamideYield 25%

Procedure

The titled compound (yield=25%, white solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 1D (Example 1) and 3,5-dimethyl-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 1.46 (s, 6H) 2.40 (s, 6H) 7.54 (d, J=8.34 Hz, 1H) 7.66 (d, J=8.34 Hz, 2H) 8.04-8.19 (m, 3H) 12.89 (br. s., 1H); ESI-MS: m/z 408.0 (M+H)+.

Sources & evidence

ORD record
ord-da816ce3ecef4b8199a9d8e50732c3bf
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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