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

HRID 1158735Notes

Reaction equation

HRID 1158735 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C:15]([CH3:17])=[CH2:16])[C:6]=2[N:18]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:6]=2[N:18]=1

Participants

5

Reactant 2

HCID 595136432-amino-9-(2-methylprop-2-en-1-yl)-9H-pyrido[2,3-b]indole-3-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 249008702-amino-9-isobutyl-9H-pyrido[2,3-b]indole-3-carboxamideYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Amino-9-(2-methylprop-2-en-1-yl)-9H-pyrido[2,3-b]indole-3-carboxamide (xii-a, 143 mg) was dissolved in ethanol (40 mL) and placed under an argon atmosphere. 10% Palladium on carbon (26 mg) was added and the reaction placed under an atmosphere of hydrogen by repeated evacuation followed by back-filling using a balloon filled with hydrogen gas. The reaction stirred for 16 h at room temperature then the catalyst was removed by filtration through Celite® and the filtrate concentrated in vacuo. The residue was purified by silica gel chromatography (5% methanol in methylene chloride) to afford the title compound (44, 44 mg, 65%). NH4OAc standard conditions. DAD Retention time =7.45 min. M+H=283. 1H NMR (300 MHz, CDCl3): Δ 8.22 (s, 1H), 7.83 (d, J=7.3 Hz, 1H), 7.30-7.36 (m, 3H), 7.21 (br s, 1H), 6.66 (br s, 1H), 5.67 (br s, 1H), 4.07 (d, J=7.3 Hz, 1H), 2.28-2.42 (m, 1H), 0.94 (d, J=6.7 Hz, 6H).

Workup

  1. customthe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-7b781a7c9e0a46dab5b66ca58566ea8d
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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