4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 4-(2-hydroxypropan-2-yl)-N-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamide

HRID 1924780Notes

Reaction equation

HRID 1924780 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.CC1(C)C(C)(C)OB([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)O1>>[OH:22][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:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[N:7]=3)=[O:23])=[CH:14][CH:15]=1)([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 58015365N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide

Product 1

HCID 445487724-(2-hydroxypropan-2-yl)-N-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamideYield 26%

Procedure

The titled compound (yield=26%, white solid) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except that 1D (Example 1) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (s, 6H) 7.68 (d, J=8.34 Hz, 2H) 8.12 (d, J=8.34 Hz, 2H) 8.29-8.46 (m, 4H) 8.87 (br. s., 2H) 13.15 (br. s., 1H); ESI-MS: m/z 391.0 (M+H)+.

Sources & evidence

ORD record
ord-4e645ad6424b44e385c772b3af234545
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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