Ammonium formate → HCID 59508043, compound

HRID 1958648Notes

Reaction equation

C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[C:23]2[C:24]([O:29][CH3:30])=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:30][O:29][C:24]1[C:23]([C:15]2[NH:16][C:17]3[C:22]([C:14]=2[CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-(2-methoxy-pyridin-3-yl)-1H-indole (0.53 g, 1.34 mmol), 10% Pd/C (50 mg), and ammonium formate (0.85 g, 13.4 mmol) were combined in methanol (100 ml) and heated at 60° C. for 2 h. The reaction was cooled, filtered through celite, and the filter cake washed with methanol. The solvent was removed under reduced pressure to give the desired product as a yellow foamy solid (0.56 g, qunatitative) which could be used in the next reaction without any further purification or purified by reverse phase chromatography. M.p.=110-115° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.11 (s, 1H, indole-NH), 8.58 (brs, 1H, NHHCl), 8.48 (brs, 1H, NHHCl), 8.26 (dd, J1=2.0 Hz, J2=4.8 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.75 (dd, J1=2.0 Hz, J2=7.6 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.14 (dd, J1=5.2 Hz, J2=7.6 Hz, 1H), 7.10 (m, 1H), 7.00 (m, 1H), 3.94 (s, 3H), 3.37 (m, 2H), 2.96 (m, 2H), 2.83 (m, 1H), 2.34 (m, 2H), 1.82 (m, 2H); LCMS: 308.65 [M+H].

Workup

temperatureThe reaction was cooled
filtrationfiltered through celite
washthe filter cake washed with methanol
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-dd215963420b4600a72f0c123d97357d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410144B2

Reaction notes

Loading…