Phenylboronic Acid → 6-Bromo-3-phenyl-imidazo[1,2-a]pyridine

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](I)=[CH:9][N:10]=2)[CH:7]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][N:10]=2)[CH:7]=1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 220316326-Bromo-3-iodoimidazo(1,2-a)pyridine

Product 1

HCID 529368446-Bromo-3-phenyl-imidazo[1,2-a]pyridine

Procedure

The title compound, off-white solid (0.4 g, 68%), MS (ISP) m/z=273.4 [(M+H)+], mp 77° C., was prepared in accordance with the general method of intermediate E from commercially available 6-bromo-3-iodoimidazo[1,2-a]pyridine (0.7 g, 2.17 mmol) and commercially available phenylboronic acid (0.29 g, 2.38 mmol).

Sources & evidence

ORD record: ord-a0021a64a2a4410ba9a3fd75066a4e0e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315502B2

Reaction notes

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