(Pyrimidin-5-yl)boronic acid → HCID 24874778, compound

HRID 2264757Notes

Reaction equation

HRID 2264757 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][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:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1>>[CH2:24]([C:20]1[CH:19]=[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:23]=[CH:22][N:21]=1)[CH3:25]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59596298HCID 59596298, compound

Product 1

HCID 24874778HCID 24874778, compoundYield 58%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-ethylpyridin-4-yl)-1H-isoindol-3-amine (Example 110) 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), 8.28 (d, J=5.30 Hz, 1 H), 7.86 (dd, J=6.06, 1.77 Hz, 1 H), 7.80-7.68 (m, 1 H), 7.64-7.54 (m, 2 H), 7.47-7.36 (m, 4 H), 7.19-7.10 (m, 1 H), 7.07 (dd, J=5.18, 1.64 Hz, 1 H), 6.85 (br s, 2 H), 2.59 (q, J=7.58 Hz, 2 H), 1.08 (t, J=7.58 Hz, 3 H); MS (ESI) m/z 392 [M+1]+.

Sources & evidence

ORD record
ord-c4269414115645c38182934ee04ebcbe
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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