4-Chloro-3-fluorophenylboronic Acid → HCID 118341178, compound

HRID 925789Notes

Reaction equation

HRID 925789 reaction equation
Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[CH:7][C:6]=2[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[F:28]>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=2)=[CH:21][C:20]=1[F:28]

Participants

3

Reactant 2

HCID 27786564-Chloro-3-fluorophenylboronic AcidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 118341178HCID 118341178, compound

Procedure

The title compound, light brown solid (64 mg, 75%), MS (ISP) m/z=340.3 [(M+H)+], mp 309° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 15) (72.5 mg, 0.25 mmol) and commercially available 4-chloro-3-fluoro-phenylboronic acid (56.7 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-2baf4f31952349fb8b8642f2b80b91b6
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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