(4-Methoxyphenyl)boronic acid → HCID 73335108, compound

HRID 925689Notes

Reaction equation

HRID 925689 reaction equation
Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]3=[C:7]([CH3:17])[C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[Cl:18][C:4]1[CH:3]=[C:2]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[C:10]2[N:9]3[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]3=[C:7]([CH3:17])[C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 90035933HCID 90035933, compound2×

Product 1

HCID 73335108HCID 73335108, compound

Procedure

The title compound, off-white solid (81 mg, 91%), MS (ISP) m/z=355.4 [(M+H)+], mp 240.5° C., was prepared in accordance with the general method of example 1 from 7-bromo-9-chloro-11-methyl-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one (intermediate 13) (81.9 mg, 0.25 mmol) and commercially available 4-methoxy-phenylboronic acid (49.4 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-1872a5997bba48f1a2c86fe633218c08
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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