(Pyrimidin-5-yl)boronic acid → HCID 24874780, compound

HRID 2264759Notes

Reaction equation

HRID 2264759 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[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:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1>>[CH:24]([C:20]1[CH:19]=[C:18]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:31]4[CH:32]=[N:27][CH:28]=[N:29][CH:30]=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)([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59596314HCID 59596314, compound

Product 1

HCID 24874780HCID 24874780, compoundYield 58%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-isopropylpyridin-4-yl)-1H-isoindol-3-amine (Example 113) as described in Example 67 Scheme #10, D in 58% yield using pyrimidine-5-boronic acid. 1H NMR (DMSO-d6) δ 9.11 (s, 1 H), 8.93 (s, 2 H), 8.30 (d, J=5.30 Hz, 1 H), 7.90-7.82 (m, 1 H), 7.81-7.69 (m, 1 H), 7.65-7.53 (m, 2 H), 7.49-7.33 (m, 4 H), 7.17-7.11 (m, 1 H), 7.07 (dd, J=5.31, 1.77 Hz, 1 H), 6.86 (br s, 2 H), 2.97-2.75 (m, 1 H), 1.08 (d, J=6.82 Hz, 6 H); MS (ESI) m/z 406 [M+1]+.

Sources & evidence

ORD record
ord-b5951c98e17a447b9ade9727cdf71763
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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