(3-Methylpyridin-4-yl)boronic acid → HCID 44548776, compound

HRID 1924776Notes

Reaction equation

HRID 1924776 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.[CH3:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1B(O)O>>[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:31]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[CH3:25])[N:7]=3)=[O:24])=[CH:14][CH:15]=1)([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 44754762(3-Methylpyridin-4-yl)boronic acidHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Product 1

HCID 44548776HCID 44548776, compoundYield 70%

Procedure

The titled compound (yield=70%) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 2F (Example 2) and 3-methylpyridin-4-ylboronic acid were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (s, 6H) 2.47 (s, 3H) 3.42 (s, 2H) 7.52 (d, J=8.59 Hz, 2H) 7.81-7.90 (m, 2H) 8.04 (d, J=8.59 Hz, 2H) 8.26 (d, J=8.34 Hz, 1H) 8.69 (d, J=4.29 Hz, 1H) 8.75 (br. s., 1H) 13.05 (br. s., 1H); ESI-MS: m/z 419.0 (M+H)+.

Sources & evidence

ORD record
ord-be4c5f07bf1f46a8a1696aeda35ee6ae
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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