N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide → HCID 178450177, compound

HRID 1924783Notes

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.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[CH:35][C:36]([OH:39])=[N:37][CH:38]=2)O1>>[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:33]2[CH:38]=[N:37][C:36]([OH:39])=[CH:35][CH:34]=2)[N:7]=3)=[O:24])=[CH:14][CH:15]=1)([CH3:23])[CH3:22]

Participants

Reactant 2

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

HCID 178431084HCID 178431084, compound

Product 1

HCID 178450177HCID 178450177, compoundYield 21%

Procedure

The titled compound (yield=21%, tan solid) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except 2F (Example 2) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 3.48 (s, 2H) 6.48 (d, J=9.60 Hz, 1H) 7.58 (d, J=8.84 Hz, 2H) 7.96 (d, J=8.59 Hz, 1H) 8.09 (d, J=8.59 Hz, 2H) 8.14 (d, J=8.59 Hz, 1H) 8.20 (d, J=2.27 Hz, 1H) 8.27 (dd, J=9.60, 2.78 Hz, 1H) 11.99 (br. s., 1H) 12.93 (br. s., 1H); ESI-MS: m/z 421.0 (M+H)+.

Sources & evidence

ORD record: ord-cda15f94f34e414e875f62143de75567
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178555B2

Reaction notes

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