(Pyrimidin-5-yl)boronic acid → 1-(2-Methoxypyrimidin-5-yl)-1-(3-pyrimidin-5-ylphenyl)-1H-isoindol-3-amine

HRID 2264755Notes

Reaction equation

HRID 2264755 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:19]=[N:20][C:21]([O:24][CH3:25])=[N:22][CH:23]=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:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1>>[CH3:25][O:24][C:21]1[N:22]=[CH:23][C:18]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:30]4[CH:31]=[N:26][CH:27]=[N:28][CH:29]=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:19][N:20]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59596264HCID 59596264, compound

Product 1

HCID 248747401-(2-Methoxypyrimidin-5-yl)-1-(3-pyrimidin-5-ylphenyl)-1H-isoindol-3-amineYield 54%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-methoxypyrimidin-5-yl)-1H-isoindol-3-amine (Example 106) as described in Example 67 Scheme #10, D in 54% yield using pyrimidine-5-boronic acid. 1H NMR (DMSO-d6) δ 9.18 (s, 1 H), 9.05 (s, 2H), 8.55 (s, 2 H), 7.98-8.11 (m, 1 H), 7.79-7.88 (m, 1 H), 7.70-7.77 (m, 1 H), 7.67 (d, J=7.58 Hz, 1 H), 7.41-7.57 (m, 4 H), 6.96 (br s, 2 H), 3.87 (s, 3 H); MS (ESI) m/z 395 [M+1]+.

Sources & evidence

ORD record
ord-8163ff9e54534c1286aff04d5ba0cc08
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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