3-Fluoro-4-methylbenzeneboronic acid → HCID 118341144, compound

HRID 925868Notes

Reaction equation

HRID 925868 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[CH3:26]>>[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[CH3:26]

Participants

3

Reactant 2

HCID 27826743-Fluoro-4-methylbenzeneboronic acidHCID 90035869HCID 90035869, compound2×

Product 1

HCID 118341144HCID 118341144, compound

Procedure

The title compound, light grey solid (75 mg, 90%), MS (ISP) m/z=334.5 [(M+H)+], mp 250.5° 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-fluoro-4-methyl-phenylboronic acid (50.0 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-d65bf9a8789f4063a8416faad4701a63
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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