3-Fluoro-4-methylbenzeneboronic acid → HCID 118341129, compound

HRID 925723Notes

Reaction equation

HRID 925723 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]([Cl:17])[CH:3]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[CH3:25]>>[Cl:17][C:4]1[CH:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:19]([F:18])[CH:20]=2)[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]=1

Participants

3

Reactant 2

HCID 27826743-Fluoro-4-methylbenzeneboronic acidHCID 90036013HCID 90036013, compound2×

Product 1

HCID 118341129HCID 118341129, compound

Procedure

The title compound, off-white solid (69 mg, 81%), MS (ISP) m/z=343.4 [(M+H)+], mp 225° C., was prepared in accordance with the general method of example 1 6-bromo-8-chloro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 12) (78.4 mg, 0.25 mmol) and commercially available 3-fluoro-4-methyl-phenylboronic acid (50.0 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-bd3cca0ed272448a9420541d0b8feba7
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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