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

HRID 1471789
Notes
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Reaction equation

HRID 1471789 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 86649942(1-(Trifluoromethyl)cyclopropyl)methyl methanesulfonateHCID 866945755-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

Product 1

HCID 717367215-(2-Fluoro-4-methanesulfonyl-phenyl)-2-[1-(1-trifluoromethyl-cyclopropylmethyl)-piperidin-4-yl]-furo[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. concentrationconcentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes