Potassium Carbonate → 5-(2-Fluoro-4-methanesulfonyl-phenyl)-2-[1-(1-trifluoromethyl-cyclopropylmethyl)-piperidin-4-yl]-furo[2,3-c]pyridine

HRID 1471789Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[CH:20]=[C:19]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:18][C:15]2=[CH:16][N:17]=1.[F:27][C:28]([F:39])([F:38])[C:29]1([CH2:32]OS(C)(=O)=O)[CH2:31][CH2:30]1.C([O-])([O-])=O.[K+].[K+].CN1CCCC1=O>O>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[CH:20]=[C:19]([CH:21]3[CH2:26][CH2:25][N:24]([CH2:32][C:29]4([C:28]([F:39])([F:38])[F:27])[CH2:31][CH2:30]4)[CH2:23][CH2:22]3)[O:18][C:15]2=[CH:16][N:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-(2-fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine (80 mg), methanesulfonic acid 1-trifluoromethyl-cyclopropylmethyl ester (120 mg), KI (21 mg), K2CO3 (92 mg), and N-methylpyrrolidinone (3 mL) is stirred at 100° C. for 4 h. After cooling to room temperature, water is added and the mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1) to give the title compound. Mass spectrum (ESI+): m/z=497 [M+H]+.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture is extracted with ethyl acetate
dry with materialThe combined extracts are dried (Na2SO4)
concentrationconcentrated
customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1)

Sources & evidence

ORD record: ord-c4a27624bb80471487031fd73953f922
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012456B2

Reaction notes

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