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Sodium Carbonate → 4-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine

HRID 1622224
Notes
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Reaction equation

HRID 1622224 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH:10]3[CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12][CH2:11]3)[CH2:7][C:6]=2[CH:22]=1.[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(=[O:26])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][CH:8]([CH:10]4[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]4)[CH2:7][C:6]=3[CH:22]=2)=[CH:29][CH:28]=1)(=[O:26])=[O:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 866748871-[4-(5-Bromo-2,3-dihydro-benzofuran-2-yl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 679732894-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1-[4-(5-bromo-2,3-dihydro-benzofuran-2-yl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone (2.50 g) and 4-(methanesulfonyl)phenyl boronic acid (1.45 g) in N,N-dimethylformamide (25 mL) a 2 M aqueous Na2CO3 solution (8.26 mL) is added. The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene].CH2Cl2 complex (540 mg) is added. The resulting mixture is stirred over night at 90° C. After cooling to room temperature, water (50 mL) and ethyl acetate (100 mL) are added and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water and brine, dried (MgSO4), and the solvent is evaporated. The residue is chromatographed on silica gel [dichloromethane/(methanol/NH4OH 9:1) 90:10-80:20] to give the title compound, since the trifluoroacetyl group is removed under the reaction conditions. LC (method 1): tR=0.88 min; Mass spectrum (ESI+): m/z=358 [M+H]+.

Workup

  1. additionis added
  2. customThe mixture is sparged with argon for 10 min
  3. additionCH2Cl2 complex (540 mg) is added
  4. temperatureAfter cooling to room temperature
  5. additionwater (50 mL) and ethyl acetate (100 mL) are added
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. washThe organic phase is washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent is evaporated
  10. customThe residue is chromatographed on silica gel [dichloromethane/(methanol/NH4OH 9:1) 90:10-80:20]

Sources & evidence

ORD record
ord-af40e06ca50547488d98f42f0d442ab4
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778926B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes