3,4-Difluorobenzeneboronic acid → HCID 73335415, compound

HRID 925832Notes

Reaction equation

HRID 925832 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=[CH:7][C:6]=2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=1.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[F:26]>>[F:19][C:20]1[CH:21]=[C:22]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=2)[CH:23]=[CH:24][C:25]=1[F:26]

Participants

3

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 90035869HCID 90035869, compound2×

Product 1

HCID 73335415HCID 73335415, compound

Procedure

The title compound, light grey solid (72 mg, 85%), MS (ISP) m/z=338.4 [(M+H)+], mp 224.5° C., was prepared in accordance with the general method of example 1 from 7-bromo-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile (intermediate 20) (76.0 mg, 0.25 mmol) and commercially available 3,4-difluoro-phenylboronic acid (51.3 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-d8fd56aa78d64581bb351eca8e1a49fc
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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