Potassium Carbonate → HCID 59127147, compound

HRID 1989918Notes

Reaction equation

HRID 1989918 reaction equation
[CH3:1][C:2]([Si:5]([CH3:28])([CH3:27])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([OH:26])[CH:25]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1)=[O:15])[CH3:9])([CH3:4])[CH3:3].[Cl:29][C:30]1[C:31](Cl)=[N:32][CH:33]=[C:34]([CH:40]=1)[C:35]([O:37][CH2:38]C)=[O:36].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:29][C:30]1[CH:40]=[C:34]([C:35]([O:37][CH3:38])=[O:36])[CH:33]=[N:32][C:31]=1[O:26][C:24]1[CH:23]=[C:13]([C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[O:15])[CH:12]=[C:11]([O:10][C@@H:8]([CH3:9])[CH2:7][O:6][Si:5]([C:2]([CH3:3])([CH3:4])[CH3:1])([CH3:28])[CH3:27])[CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16762519Ethyl 5,6-DichloronicotinateHCID 536296323-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 59127147HCID 59127147, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (1.0 g, 2.47 mmol), ethyl 5,6-dichloronicotinate (0.57 g, 2.59 mmol), and potassium carbonate (0.855 g, 6.14 mmol) in acetonitrile (15 mL) was heated at 160° C. for 4 hours using microwave heating. The acetonitrile was removed in vaccuo and the residual oil partitioned between water (50 mL) and ethyl acetate (75 mL). The ethyl acetate layer was separated, washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with 50% ethyl acetate in hexane to give the desired compound (1.1 g). The analytical data indicated that transesterification had occurred at some stage in the procedure to furnish the methyl ester.

Workup

  1. customThe acetonitrile was removed in vaccuo
  2. customthe residual oil partitioned between water (50 mL) and ethyl acetate (75 mL)
  3. customThe ethyl acetate layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas chromatographed on silica
  8. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d1081ef8dd8145a1a53c6e9a91b6d02e
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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