4-Chlorophenylboronic acid → HCID 90035986, compound

HRID 925883Notes

Reaction equation

HRID 925883 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][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[C:22]([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:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90035986HCID 90035986, compound

Procedure

The title compound, off-white solid (70 mg, 83%), MS (ISP) m/z=336.5 [(M+H)+], mp 254° 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-phenylboronic acid (50.8 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-dd633e1252434e39af91dc614ecef734
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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