3-Bromo-2-methyl-1-propene → 2-amino-9-(2-methylprop-2-en-1-yl)-9H-pyrido[2,3-b]indole-3-carboxamide

HRID 421644Notes

Reaction equation

HRID 421644 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:14]=1.[CH2:18](Br)[C:19](=[CH2:21])[CH3:20].NC1C(C(N)=O)=CC2C3C(=CC=CC=3)N(C(C)C)C=2N=1>>[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:20][C:19]([CH3:21])=[CH2:18])[C:6]=2[N:14]=1

Participants

4

Reactant 3

HCID 3577853-Bromo-2-methyl-1-propeneHCID 152709842-amino-9H-pyrido[2,3-b]indole-3-carboxamideHCID 249006762-amino-9-isopropyl-9H-pyrido[2,3-b]indole-3-carboxamide

Product 1

HCID 595136432-amino-9-(2-methylprop-2-en-1-yl)-9H-pyrido[2,3-b]indole-3-carboxamideYield 59%

Procedure

2-Amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 196 mg, 0.866 mmol) was alkylated with methallyl bromide (0.131 mL, 1.30 mmol) according to the procedure detailed in the synthesis of 13 to afford 2-amino-9-(2-methylprop-2-en-1-yl)-9H-pyrido[2,3-b]indole-3-carboxamide (xii-a, 143 mg, 59%).

Sources & evidence

ORD record
ord-87784495542e428790c9bc096c17a66e
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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