Toluene → N-{6-[3-(pyridin-3-ylamino)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

HRID 1874557

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1.Br[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>C(=O)([O-])O.[Na+]>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:14]=3)[CH:11]=2)[CH:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (20.0 mg, 0.065 mmol), 3-bromopyridine (14.4 mg, 0.091 mmol), tris(dibenzylideneacetone)2 palladium(0) (6.8 mg, 0.0074 mmol), 5-bis(diphenylphosphino)-9,9-dimethylxanthene (4.3 mg, 0.007 mmol), potassium t-butoxide (17.2 mg, 0.153 mmol) and toluene (2.0 mL) was stirred at 120° C. for 13 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (3.0 mg, 12%).

Workup

extractionextracted with ethyl acetate
concentrationThe organic layer was concentrated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-0f688638b5fb45d78e58eb40a6e66ec0
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Linked notes

Loading…