(Pyrimidin-5-yl)boronic acid → 1-Cyclopropyl-1-(3-pyrimidin-5-ylphenyl)-1H-isoindol-3-amine acetate

HRID 2264746Notes

Reaction equation

HRID 2264746 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].Br[C:6]1[CH:7]=[C:8]([C:12]2([CH:22]3[CH2:24][CH2:23]3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH2:21])=[N:13]2)[CH:9]=[CH:10][CH:11]=1.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1>>[C:1]([OH:4])(=[O:3])[CH3:2].[CH:22]1([C:12]2([C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:29]4[CH:30]=[N:25][CH:26]=[N:27][CH:28]=4)[CH:7]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH2:21])=[N:13]2)[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 672723191-(3-Bromophenyl)-1-cyclopropyl-1H-isoindol-3-amine acetate

Product 1

HCID 248746481-Cyclopropyl-1-(3-pyrimidin-5-ylphenyl)-1H-isoindol-3-amine acetateYield 85%

Procedure

The title compound was prepared in 85% yield as described for Example 78 (Scheme #14, N) starting from 1-(3-bromophenyl)-1-cyclopropyl-1H-isoindol-3-amine acetate (Scheme #15, O) and pyrimidine-5-ylboronic acid: 1H NMR (DMSO-d6) δ 9.19 (s, 1 H), 9.10 (s, 2 H), 8.02 (t, J=1.76 Hz, 1 H), 7.77 (t, J=8.03 Hz, 2 H), 7.64 (dd, J=7.78, 1.25 Hz, 1 H), 7.60-7.55 (m, 1 H), 7.47-7.37 (m, 3 H), 2.05-1.94 (m, 1 H), 1.87 (s, 3 H), 0.52-0.41 (m, 2 H), 0.28-0.17 (m, 1 H), −0.04-0.05 (m, 1 H); MS (ES) m/z 327 [M+1]+.

Sources & evidence

ORD record
ord-eacf2ac15dfb4866be099e4280e83060
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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