(Pyrimidin-5-yl)boronic acid → HCID 24874821, compound

HRID 2264764Notes

Reaction equation

HRID 2264764 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1>>[Cl:24][C:20]1[CH:19]=[C:18]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:29]4[CH:30]=[N:25][CH:26]=[N:27][CH:28]=4)[CH:3]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:23]=[CH:22][N:21]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59596297HCID 59596297, compound

Product 1

HCID 24874821HCID 24874821, compoundYield 51%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-chloropyridin-4-yl)-1H-isoindol-3-amine (Example 120) as described in Example 67 Scheme #10, D in 51% yield using pyrimidine-5-boronic acid. 1H NMR (DMSO-d6) δ 9.18 (s, 1 H), 9.04 (s, 2 H), 8.31 (d, J=5.30 Hz, 1 H), 8.06-7.94 (m, 1 H), 7.89-7.81 (m, 1 H), 7.72-7.65 (m, 2 H), 7.57-7.45 (m, 4 H), 7.38 (dd, J=5.31, 1.52 Hz, 1 H), 7.36-7.33 (m, 1 H), 7.01 (br s, 2 H); MS (ESI) m/z 398 [M+1]+.

Sources & evidence

ORD record
ord-a82deddb6c98483c933e012fc605ce9d
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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