Water → HCID 10291189, compound

HRID 985508Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.F[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26].O>CN(C)C=O>[CH3:17][C:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[N+:25]([O-:27])=[O:26])[CH:7]=[CH:6][CH:5]=3)=[CH:9][N:10]=[C:11]2[CH:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

3-(3-Aminophenyl)-7-methylimidazo[1,2-α]pyridine (1.0 g, 4.5 mmol) and 1-fluoro-2-nitrobenzene (0.55 ml, 5.2 mmol) were dissolved in anhydrous N,N-dimethylformamide (10 ml) and heated at 120° C. for 2 days. The cooled reaction mixture was poured into water (25 ml), extracted with ethyl acetate (2×20 ml) and the combined organic phases dried over anhydrous magnesium sulphate and concentrated in vacuo. Purification by flash chromatography eluting with 5% methanol in dichloromethane gave the title compound as an orange oil (160 mg, 10%). 1H NMR (400 MHz, d4-methanol) δH 2.61 (3H, s), 6.89-6.93 (1H, m), 7.33-7.35 (1H, m), 7.40-7.42 (1H, m), 7.47-7.52 (2H, m), 7.55-7.57 (1H, m), 7.62-7.69 (2H, m), 7.74 (1H, s), 8.06 (1H, s), 8.24 (1H, d, J 7), 8.67 (1H, d, J 8); m/z (ES+) 345 (M++H).

Workup

customThe cooled reaction mixture
extractionextracted with ethyl acetate (2×20 ml)
dry with materialthe combined organic phases dried over anhydrous magnesium sulphate
concentrationconcentrated in vacuo
customPurification by flash chromatography
washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-df93a6ff3824463a821e3162d1dd36e8
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872731B2

Reaction notes

Loading…