(4-Chloro-2-fluorophenyl)boronic acid → 6-Bromo-3-(4-chloro-2-fluorophenyl)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.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[C:15]([F:22])[CH:14]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:16]3[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][C:15]=3[F:22])=[CH:9][N:10]=2)[CH:7]=1

Participants

Reactant 2

HCID 4193595(4-Chloro-2-fluorophenyl)boronic acid

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

Product 1

HCID 901894736-Bromo-3-(4-chloro-2-fluorophenyl)imidazo[1,2-a]pyridine

Procedure

The title compound, light brown solid (0.54 g, 76%), MS (ISP) m/z=327.3 [(M+H)+], mp 159° 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 4-chloro-2-fluoro-phenylboronic acid (0.42 g, 2.38 mmol).

Sources & evidence

ORD record: ord-0fa1368362cc47d2abf1d638ed1cd4c0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315502B2

Reaction notes

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