3-(Trifluoromethyl)phenylboronic acid → HCID 90036060, compound

HRID 925810Notes

Reaction equation

HRID 925810 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.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1>>[O:15]=[C:14]1[C:8]2=[CH:7][C:6]3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=[C:2]([C:24]4[CH:23]=[CH:22][CH:21]=[C:20]([C:19]([F:30])([F:29])[F:18])[CH:25]=4)[C:10]=3[N:9]2[CH2:11][CH2:12][NH:13]1

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 90036060HCID 90036060, compound

Procedure

The title compound, off-white solid (78 mg, 88%), MS (ISP) m/z=356.5 [(M+H)+], mp 279.5° 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 3-trifluoromethyl-phenylboronic acid (61.7 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-d5e5a9193f0a425583edcecae72bf353
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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