Water → 6-[2-(6-Methyl-pyridin-2-yl)-imidazo[1,2-a]pyridin-3-yl]-quinoline

HRID 2220067Notes

Reaction equation

Br[CH:2]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][CH:16]=[CH:15]2)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)=O.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.O>CN(C)C=O>[CH3:11][C:7]1[N:6]=[C:5]([C:3]2[N:22]=[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]3[C:2]=2[C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone of Step D (60 mg, 0.176 mmol)in dimethylformamide (1 mL) was treated with 2-aminopyridine (50 mg, 0.53 mmol, 3 equiv), and heated to 80° C. over 4.5 hours. After cooling down, the mixture was treated with water and extracted with ethyl acetate. The organics were concentrated in vacuo and reverse phase column chromatography (a gradient from 5-30% acetonitrile in 0.1% aqueous formic acid) provided the title compound (14.7 mg, 25%). HPLC tR=1.71 min, LCMS 337.3 (M+1).

Workup

temperatureAfter cooling down
extractionextracted with ethyl acetate
concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record: ord-81a1238ca7e145d6acacaa53de47f872
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417041B2

Reaction notes

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