(Pyrimidin-5-yl)boronic acid → HCID 59596243, compound

HRID 2264730Notes

Reaction equation

HRID 2264730 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)=[CH:3][C:2]=1[C:29]1[CH:30]=[N:25][CH:26]=[N:27][CH:28]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59596252HCID 59596252, compound

Product 1

HCID 59596243HCID 59596243, compoundYield 41%

Procedure

The title compound was synthesized from 1-(3-bromo-4-fluorophenyl)-1-pyridin-4-yl-1H-isoindol-3-amine (Scheme #11, G) as described in Example 67 (Scheme #10, D) in 41% yield using pyrimidin-5-ylboronic acid. 1H NMR (DMSO-d6) δ 9.02 (s, 1 H), 8.78-8.72 (m, 2 H), 8.30-8.23 (m, 2 H), 7.78-7.70 (m, 1 H), 7.66-7.58 (m, 1 H), 7.41-7.26 (m, 4 H), 7.20-7.08 (m, 3 H), 6.76 (br s, 2 H), 1.72 (s, 1.9 H); MS (ESI) m/z 382 [M+1]+.

Sources & evidence

ORD record
ord-84d319e8fd2c43e2bb5654ab0d597e48
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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