Dichloromethane → 7-(2-Fluoro-4-nitrophenoxy)-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine

HRID 2193652Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=3)[S:10][C:3]=12.[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[OH:27].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[O:27][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=3)[S:10][C:3]=12

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of the compound 16 (1.52 g, 6.09 mmol), 2-fluoro-4-nitrophenol (3.87 g, 24.6 mmol) and K2CO3 (4.31 g, 31.2 mmol) in Ph2O (20 mL) was heated at 190° C. overnight. DCM (250 mL) was added to the resultant dark-brown mixture, which was then extracted with aqueous 1M HCl. The aqueous layer was collected, washed with DCM and basified with NH4OH. The resultant cloudy mixture was extracted with DCM. The organic phase was combined, filtered; the filtrate was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resultant yellow solid was purified by flash chromatography, eluent EtOAc/MeOH (80:20) to afford title compound 17 as a yellow solid (0.96 g, 43% yield). MS (m/z): 371.0 (M+H).

Workup

extractionwas then extracted with aqueous 1M HCl
customThe aqueous layer was collected
washwashed with DCM and basified with NH4OH
extractionThe resultant cloudy mixture was extracted with DCM
filtrationfiltered
washthe filtrate was washed with water
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure
customThe resultant yellow solid was purified by flash chromatography, eluent EtOAc/MeOH (80:20)

Sources & evidence

ORD record: ord-b7581779452a41188a44c8351910700e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329726B2

Reaction notes

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