(Pyrimidin-5-yl)boronic acid → HCID 24874824, compound

HRID 2264768Notes

Reaction equation

HRID 2264768 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH3:27])[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:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[N:30][CH:29]=1>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH3:27])[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:32]1[CH:33]=[N:28][CH:29]=[N:30][CH:31]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59596235HCID 59596235, compound

Product 1

HCID 24874824HCID 24874824, compoundYield 41%

Procedure

The title compound was synthesized from 1-(3-bromo-4-fluorophenyl)-1-(4-methoxy-3-methylphenyl)-1H-isoindol-3-amine (Example 126) as described in Example 67 Scheme #10, D in 41% yield using pyrimidine-5-boronic acid. 1H NMR (DMSO-d6) δ 9.07 (s, 1 H), 8.78 (d, J=1.26 Hz, 2 H), 7.76-7.61 (m, 2 H), 7.43-7.24 (m, 4 H), 7.22-7.11 (m, 1 H), 7.01-6.90 (m, 2 H), 6.88-6.54 (m, 3 H), 3.58 (s, 3 H), 1.92 (s, 3 H); MS (ESI) m/z 425 [M+1]+.

Sources & evidence

ORD record
ord-740e7523bb7d451aa850e3027f9c83a5
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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