3-Cyanophenylboronic acid → HCID 90036230, compound

HRID 925884Notes

Reaction equation

HRID 925884 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.[C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:20]>>[C:19]([C:21]1[CH:26]=[C:25]([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:24]=[CH:23][CH:22]=1)#[N:20]

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 90035869HCID 90035869, compound2×

Product 1

HCID 90036230HCID 90036230, compound

Procedure

The title compound, light grey solid (78 mg, 96%), MS (ISP) m/z=327.5 [(M+H)+], mp 225.5° 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-cyanophenylboronic acid (47.8 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-d36ea45f14344cb19cbd19e27e01c6e8
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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