4-Chloro-3-fluorophenylboronic Acid → HCID 90035836, compound

HRID 925795Notes

Reaction equation

HRID 925795 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=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][C:21]=1[F:29]>>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[C:7]([CH3:16])[C:6]=3[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=2)=[CH:22][C:21]=1[F:29]

Participants

3

Reactant 2

HCID 27786564-Chloro-3-fluorophenylboronic AcidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90035836HCID 90035836, compound

Procedure

The title compound, off-white solid (63 mg, 71%), MS (ISP) m/z=354.5 [(M+H)+], mp 260° C., was prepared in accordance with the general method of example 1 from 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 16) (76 mg, 0.25 mmol) and commercially available 4-chloro-3-fluoro-phenylboronic acid (56.7 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-8d7d5b28ae674ffba841ae4adc1d1ea3
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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