5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 73335618, compound

HRID 925866Notes

Reaction equation

HRID 925866 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.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[CH:30][C:31]([NH2:34])=[N:32][CH:33]=2)O1>>[NH2:34][C:31]1[N:32]=[CH:33][C:28]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]4=[C:7]([CH3:17])[C:6]=3[CH:5]=[C:4]([C:18]#[N:19])[CH:3]=2)=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 90036394HCID 90036394, compound2×

Product 1

HCID 73335618HCID 73335618, compound

Procedure

The title compound, off-white solid (28 mg, 34%), MS (ISP) m/z=332.4 [(M+H)+], mp 306° 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 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-5031d3a881ef4615955be934cd0c0c21
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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