2-Acetamidopyridine-5-boronic acid pinacol ester → N-(5-(6-acetamidopyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

HRID 1924779Notes

Reaction equation

HRID 1924779 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[N:13][CH:14]=2)O1.Br[C:21]1[N:26]=[C:25]2[S:27][C:28]([NH:30][C:31](=[O:43])[C:32]3[CH:37]=[CH:36][C:35]([C:38]([CH3:42])([CH3:41])[CH2:39][OH:40])=[CH:34][CH:33]=3)=[N:29][C:24]2=[CH:23][CH:22]=1>>[C:16]([NH:15][C:12]1[N:13]=[CH:14][C:9]([C:21]2[N:26]=[C:25]3[S:27][C:28]([NH:30][C:31](=[O:43])[C:32]4[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:42])[CH2:39][OH:40])=[CH:34][CH:33]=4)=[N:29][C:24]3=[CH:23][CH:22]=2)=[CH:10][CH:11]=1)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 177502022-Acetamidopyridine-5-boronic acid pinacol esterHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Product 1

HCID 44548773N-(5-(6-acetamidopyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamideYield 14%

Procedure

The titled compound (yield=14%, white solid) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide and 2F (Example 2) were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 2.14 (s, 3H) 3.49 (d, J=5.31 Hz, 2H) 4.78 (t, J=5.31 Hz, 1H) 7.58 (d, J=8.59 Hz, 2H) 8.06-8.18 (m, 3H) 8.18-8.26 (m, 2H) 8.52 (dd, J=8.84, 2.53 Hz, 1H) 9.09 (d, J=1.77 Hz, 1H) 10.73 (s, 1H) 13.00 (s, 1H); ESI-MS: m/z 462.0 (M+H)+.

Sources & evidence

ORD record
ord-eeb9de39980c42a2b77121a66d03d59e
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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