Ammonium Chloride → 1-[4-(6-Bromo-3H-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-pyrrolidin-1-ylpropan-2-ol

HRID 2218371Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]4[CH2:21][O:20]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]([OH:20])[CH2:21][N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 6-bromo-2-[4-(oxiran-2-ylmethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (119 mg, 0.35 mmol) in DMF (8 ml), pyrrolidine (144 μl, 1.73 mmol) was added. The mixture was heated at 85° C. for 10 h. 5% Aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic phase was filtered and concentrated. Purification by flash chromatography on silica using methylene chloride/methanol/ammonia as eluent afforded the title compound (35 mg, 24%).

Workup

extractionthe mixture was extracted with ethyl acetate
filtrationThe organic phase was filtered
concentrationconcentrated
customPurification by flash chromatography on silica

Sources & evidence

ORD record: ord-33af62ab8c3d4f33833023ccaa4343c7
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410966B2

Reaction notes

Loading…