Bromide ion → HCID 86297147, compound

HRID 930831Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([NH:18][C:19](=[O:25])[O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:14]=[CH:15][C:16]=3[Cl:17])[N:10]=2)[CH:7]=1.[Br-].[CH3:27][O:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)=[O:30]>>[Cl:17][C:16]1[CH:15]=[CH:14][C:13]([NH:18][C:19](=[O:25])[O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:12][C:11]=1[C:9]1[N:10]=[C:5]2[N:4]=[CH:3][C:2]([C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:29]([O:28][CH3:27])=[O:30])=[CH:37][CH:36]=3)=[CH:7][N:6]2[CH:8]=1

Participants

Reactant 3

HCID 259Bromide ion

HCID 27734944-(Methoxycarbonylamino)phenylboronic acid

HCID 90444848HCID 90444848, compound

Product 1

HCID 86297147HCID 86297147, compound

Procedure

Compound 32 was synthesized using 2-methoxyethyl (3-(6-bromoimidazo[1,2-a]pyrimidin-2-yl)-4-chlorophenyl)carbamate (I-12) as the bromide and (4-((methoxycarbonyl)amino)phenyl)boronic acid using a suzuki coupling procedure described in I-13. Purification of the compound was done via mass-triggered reverse phase column chromatography preparative system (15% to 65% (B)). m/z (ESI) for 32: 496 (M+H+), 1H NMR (600 MHz, DMSO-D6) δ 10.01 (s, 1H), 9.86 (s, 1H), 9.30 (s, 1H), 8.95 (s, 1H), 8.55 (s, 1H), 8.47 (s, 1H), 7.72 (d, J=6.0, 2H), 7.62 (d, J=6.6, 2H), 7.50 (dt, J=5.7, 8.5, 2H), 4.24 (s, 2H), 3.70 (s, 3H), 3.59 (s, 2H), 3.30 (s, 3H).

Workup

customPurification of the compound

Sources & evidence

ORD record: ord-70b874e276074920ac8078101685a55a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296754B2

Reaction notes

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