5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 90036556, compound

HRID 925879Notes

Reaction equation

HRID 925879 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.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[CH:29][C:30]([NH2:33])=[N:31][CH:32]=2)O1>>[NH2:33][C:30]1[N:31]=[CH:32][C:27]([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:28][CH:29]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 90035869HCID 90035869, compound2×

Product 1

HCID 90036556HCID 90036556, compound

Procedure

The title compound, brown solid (46 mg, 58%), MS (ISP) m/z=318.5 [(M+H)+], mp 314.5° 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 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-amine (71.5 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-d07095bfd01c48b0ba56bc13e24bdf36
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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