Sodium Carbonate → HCID 58123831, compound

HRID 1616656Notes

Reaction equation

HRID 1616656 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:21][CH2:20][C:19]2([CH3:25])[C:22]([CH3:24])([CH3:23])[CH:15]1[CH2:16][C:17]1[CH:29]=[C:28](OS(C(F)(F)F)(=O)=O)[CH:27]=[CH:26][C:18]=12)=[O:13])([CH3:10])([CH3:9])[CH3:8].[C:38]1(B(O)O)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C)C=O>[C:7]([O:11][C:12]([N:14]1[CH2:21][CH2:20][C:19]2([CH3:25])[C:22]([CH3:23])([CH3:24])[CH:15]1[CH2:16][C:17]1[CH:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:27]=[CH:26][C:18]=12)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58123924HCID 58123924, compound

Product 1

HCID 58123831HCID 58123831, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Aqueous 2 M Na2CO3 solution (5 mL) is added to a mixture of 6,11,11-trimethyl-9-trifluoromethanesulfonyloxy-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester (1.00 g) and phenylboronic acid (0.34 g) in N,N-dimethylformamide (5 mL) in argon atmosphere. The resulting mixture is flushed with argon and then 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.18 g) is added. The mixture is heated to 100° C. and stirred at this temperature for 4 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are dried (MgSO4) and the solvent is removed under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1→1:1) to give the product as a colorless oil.

Workup

  1. customThe resulting mixture is flushed with argon
  2. addition1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.18 g) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater is added
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. dry with materialThe combined organic extracts are dried (MgSO4)
  7. customthe solvent is removed under reduced pressure
  8. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1→1:1)

Sources & evidence

ORD record
ord-c46c8ef80c6f4c31846d5a45da4cc024
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

Loading…