Sodium Carbonate → HCID 71208354, compound

HRID 1622248Notes

Reaction equation

HRID 1622248 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:18][C:17]3[CH:19]=[C:20](Br)[CH:21]=[CH:22][C:16]=3[O:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:24][O:25][C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)=[O:27].C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH3:24][O:25][C:26](=[O:27])[C:28]1[CH:33]=[CH:32][C:31]([C:20]2[CH:21]=[CH:22][C:16]3[O:15][CH:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH2:18][C:17]=3[CH:19]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 67973252HCID 67973252, compound

Product 1

HCID 71208354HCID 71208354, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-(5-bromo-2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.00 g) and 4-(methoxycarbonyl)phenyl boronic acid (565 mg) in N,N-dimethylformamide (50 mL) a 2 M aqueous Na2CO3 solution (3.27 mL) is added. The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene].CH2Cl2 complex (213 mg) is added. The resulting mixture is stirred for 5 h 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 over MgSO4, and the solvent is evaporated. The residue is mixed with trifluoroacetic acid (1.4 mL), dichloromethane (1.4 mL), and water (0.15 mL) and stirred for 3 h. The solvents are evaporated and the residue is mixed with diethyl ether. The title compound is collected by filtration as the trifluoroacetic acid salt. LC (method 8): tR=1.19 min; Mass spectrum (ESI+): m/z=338 [M+H]+.

Workup

  1. additionis added
  2. customThe mixture is sparged with argon for 10 min
  3. additionCH2Cl2 complex (213 mg) is added
  4. temperatureAfter cooling to room temperature water (50 mL) and ethyl acetate (100 mL)
  5. additionare added
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. washThe organic phase is washed with water and brine
  8. dry with materialdried over MgSO4
  9. customthe solvent is evaporated
  10. additionThe residue is mixed with trifluoroacetic acid (1.4 mL), dichloromethane (1.4 mL), and water (0.15 mL)
  11. stirringstirred for 3 h
  12. customThe solvents are evaporated
  13. additionthe residue is mixed with diethyl ether
  14. filtrationThe title compound is collected by filtration as the trifluoroacetic acid salt

Sources & evidence

ORD record
ord-ce894a6ffb6d4fa8b612a6e5dfa2ba24
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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