Sodium Carbonate → HCID 11951661, compound

HRID 1766468Notes

Reaction equation

HRID 1766468 reaction equation
[CH2:1]([O:8][C:9]1[C:24](Br)=[CH:23][C:12]([C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O>[CH2:1]([O:8][C:9]1[C:24]([C:30]2[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=2)=[CH:23][C:12]([C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 68811873HCID 68811873, compound

Product 1

HCID 11951661HCID 11951661, compoundYield 55.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 6-benzyloxy-5-bromo-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide (85 mg) in 1,2-dimethoxyethane (1.6 ml) was added tetrakis(triphenyl-phosphine)palladium(0) (24.5 mg). The mixture was stirred for 10 min. 4-chlorophenyl-boronic acid (37.2 mg) was dissolved in 0.7 ml EtOH and added to the reaction mixture. A solution of Na2CO3 (190 mg) in water (1 ml) was added. The reaction mixture was stirred at 85° C. for 3 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with brine. The org. phase was dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2MeOH 4:1) to give 6-benzyloxy-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide (50.6 mg) as a white solid. MS (ISP) 437.2 (M+H)+.

Workup

  1. additionadded to the reaction mixture
  2. stirringThe reaction mixture was stirred at 85° C. for 3 h
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with brine
  7. customphase was dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2MeOH 4:1)

Sources & evidence

ORD record
ord-07154456c2234b20932e93d927e275bb
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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