Cesium carbonate → HCID 24900869, compound

HRID 421650Notes

Reaction equation

HRID 421650 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.[CH3:18][C:19]1([O:22][CH2:21]1)[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[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]([CH2:18][C:19]([OH:22])([CH3:21])[CH3:20])[C:6]=2[N:14]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11208Isobutylene oxideHCID 152709842-amino-9H-pyrido[2,3-b]indole-3-carboxamide

Product 1

HCID 24900869HCID 24900869, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 200 mg, 0.884 mmol), isobutylene oxide (0.196 mL, 2.21 mmol) and cesium carbonate (460 mg, 1.40 mmol) in N,N-dimethylformamide (2.5 mL) were stirred at 100° C. under microwave irradiation for 10 min. The volatiles were removed in vacuo then the crude residue was adsorbed onto silica gel using methanol and purified by silica gel chromatography (5-10% methanol in methylene chloride gradient) to afford the title compound (43, 185 mg, 70%). NH4OAc standard conditions. DAD Retention time=5.93 min. M+H=299. 1H NMR (300 MHz, MeOD-d4): 8.64 (d, J=4.9 Hz, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.34 (dd, J=7.6, 7.3 Hz, 1H), 7.20 (dd, J=7.8, 7.3 Hz, 1H), 5.49 (s, 2H), 1.28 (s, 6H).

Workup

  1. customThe volatiles were removed in vacuo
  2. custompurified by silica gel chromatography (5-10% methanol in methylene chloride gradient)

Sources & evidence

ORD record
ord-6e998e0b80d74f12aa1151bf2ba314c7
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

Loading…