(Pyrimidin-5-yl)boronic acid → HCID 73335895, compound

HRID 925914Notes

Reaction equation

HRID 925914 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]([C:18]#[N:19])[CH:3]=1.[N:20]1[CH:25]=[C:24](B(O)O)[CH:23]=[N:22][CH:21]=1>>[CH3:17][C:7]1[C:6]2[CH:5]=[C:4]([C:18]#[N:19])[CH:3]=[C:2]([C:24]3[CH:25]=[N:20][CH:21]=[N:22][CH:23]=3)[C:10]=2[N:9]2[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]=12

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 90036394HCID 90036394, compound2×

Product 1

HCID 73335895HCID 73335895, compound

Procedure

The title compound, light yellow solid (19 mg, 24%), MS (ISP) m/z=318.6 [(M+H)+], mp 304° C., was prepared in accordance with the general method of example 1 from 7-bromo-11-methyl-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile (intermediate 17) (79.5 mg, 0.25 mmol) and commercially available pyrimidin-5-ylboronic acid (40.3 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-33a06d93ed33403687e2fce1c7cd27e9
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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