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Sodium Carbonate → 4-[5-(4-Methanesulfonyl-phenyl)-benzofuran-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 533111
Notes
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Reaction equation

HRID 533111 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26](Br)=[CH:25][C:23]=3[CH:24]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)(=[O:33])=[O:32]>O1CCOCC1.O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26]([C:37]4[CH:38]=[CH:39][C:34]([S:31]([CH3:30])(=[O:33])=[O:32])=[CH:35][CH:36]=4)=[CH:25][C:23]=3[CH:24]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 86686878HCID 86686878, compound

Product 1

HCID 866868794-[5-(4-Methanesulfonyl-phenyl)-benzofuran-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)
Solvent

Conditions

Temperature
100 °C

Procedure

An aqueous Na2CO3 solution (2 M, 0.68 mL) is added to a mixture of 4-(5-bromo-benzofuran-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (2.50 g) and 4-(methanesulfonyl)phenylboronic acid (1.97 g) in a mixture of dioxane/water (60:40). The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (500 mg) is added. The resulting mixture is heated to 100° C. for 2 h. After cooling to room temperature, ethyl acetate, brine, and activated charcoal are added. The mixture is filtered and the organic phase is separated, dried over Na2SO4, and the solvent is evaporated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40) to give the title compound. LC (method 1): tR=1.80 min; Mass spectrum (ESI+): m/z=478 [M+Na]+.

Workup

  1. customThe mixture is sparged with argon for 10 min
  2. additionPdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (500 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionethyl acetate, brine, and activated charcoal are added
  5. filtrationThe mixture is filtered
  6. customthe organic phase is separated
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated
  9. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40)

Sources & evidence

ORD record
ord-edc422d760b44037808d4fd0f950866c
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853239B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes