5-Fluoro-2-hydroxyphenylboronic acid → HCID 135965690, compound

HRID 1185399Notes

Reaction equation

HRID 1185399 reaction equation
[NH2:1][C:2]1[S:6][C:5](Br)=[N:4][C:3]=1[C:8]([NH:10][C:11]1[CH:12]=[N:13][N:14]([CH3:34])[C:15]=1[N:16]1[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23]C(=O)OCC2C=CC=CC=2)[CH2:18][CH2:17]1)=[O:9].[F:35][C:36]1[CH:37]=[CH:38][C:39]([OH:45])=[C:40](B(O)O)[CH:41]=1>>[NH2:1][C:2]1[S:6][C:5]([C:38]2[CH:37]=[C:36]([F:35])[CH:41]=[CH:40][C:39]=2[OH:45])=[N:4][C:3]=1[C:8]([NH:10][C:11]1[CH:12]=[N:13][N:14]([CH3:34])[C:15]=1[N:16]1[CH2:22][CH2:21][CH2:20][C@@H:19]([NH2:23])[CH2:18][CH2:17]1)=[O:9]

Participants

3

Reactant 2

HCID 37724765-Fluoro-2-hydroxyphenylboronic acidHCID 86658427HCID 86658427, compound

Product 1

HCID 135965690HCID 135965690, compoundYield 21%

Procedure

Following Example 278, Suzuki coupling of (R)-benzyl 1-(4-(5-amino-2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)azepan-4-ylcarbamate and 5-fluoro-2-hydroxyphenylboronic acid gave 357 as a yellow solid (12 mg, 21% over two steps). 1H NMR (400 MHz, d6-DMSO with D2O) δ 7.80 (dd, J=10.1, 3.3 Hz, 1H), 7.42 (s, 1H), 6.94 (td, J=8.5, 3.4 Hz, 1H), 6.77 (dd, J=9.0, 4.9 Hz, 1H), 3.63 (s, 3H), 3.23-3.04 (m, 6H), 1.93-1.76 (m, 3H), 1.68-1.51 (m, 3H). LCMS (ES+) m/z 446 (M+1)

Sources & evidence

ORD record
ord-c224baa93f57491d8f1321c3846350b9
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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