2-Fluoropyridine-4-boronic acid → N-(5-(2-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

HRID 1924781Notes

Reaction equation

HRID 1924781 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.[F:25][C:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[CH:28][N:27]=1>>[F:25][C:26]1[CH:31]=[C:30]([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:29]=[CH:28][N:27]=1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Product 1

HCID 44548622N-(5-(2-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamideYield 38%

Procedure

The titled compound (yield=38%, light yellow solid) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except that 2F (Example 2) and 2-fluoropyridin-4-ylboronic acid were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 3.49 (d, J=3.03 Hz, 2H) 4.78 (br. s., 1H) 7.59 (d, J=8.59 Hz, 2H) 7.91 (s, 1H) 8.06-8.16 (m, 3H) 8.27-8.36 (m, 2H) 8.38 (d, J=5.31 Hz, 1H) 13.11 (s, 1H); ESI-MS: m/z 423.0 (M+H)+.

Sources & evidence

ORD record
ord-7e90e06b241e4df395853686b3f988a5
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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