Triethylamine → N-Cyclohexyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 1821806Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([NH:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:12])[NH:8][C:7]=12.C(N(CC)CC)C>CN(C)C=O.[Pd](Cl)Cl>[CH:14]1([NH:13][C:11]([C:9]2[NH:8][C:7]3=[CH:2][N:3]=[CH:4][CH:5]=[C:6]3[CH:10]=2)=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

7-Chloro-N-cyclohexyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (230 mg, 0.828 mmol), triethylamine (0.25 mL) and palladium(II)chloride (3 mg, 2 mol %) were combined in N,N-dimethylformamide (5 mL) under an atmosphere of hydrogen. The reaction mixture was heated at 60° C. for 3 h. The reaction mixture was cooled to room temperature and the catalyst was removed by filtration through a pad of diatomaceous earth and washed with ethyl acetate. Evaporation of the solvents provided crude product (169 mg, 84%) as an off-white solid. Purification by chromatography (SiO2; 0-10% methanol in methylene chloride, 1400 mL) afforded N-cyclohexyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (101 mg, 0.414 mmol, 50%) as fine, white needles: mp 298-301° C., 1H NMR (300 MHz, CD3OD) δ 1.20-1.55 (6H, m), 1.65-2.10 (4H, m), 3.90 (1H, m), 7.21 (1H, s), 7.15 (1H, s), 7.65 (1H, d, J=5.7 Hz), 8.09 (1H, d, J=5.7 Hz), 8.77 (1H, s); ESI MS m/z 244 [C14H17N3O+H]+; HPLC (Method A) >99% (AUC), tR=13.2 min.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe catalyst was removed by filtration through a pad of diatomaceous earth
washwashed with ethyl acetate
customEvaporation of the solvents
customprovided crude product (169 mg, 84%) as an off-white solid
customPurification by chromatography (SiO2; 0-10% methanol in methylene chloride, 1400 mL)

Sources & evidence

ORD record: ord-1ff14f64c1f04ba5a981f301343f8884
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

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