Cesium carbonate → HCID 59127148, compound

HRID 1989911Notes

Reaction equation

HRID 1989911 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[C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][N:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][C:2]([Si:5]([CH3:28])([CH3:27])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:25]=[C:24]([O:26][C:30]2[N:31]=[CH:32][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:38][CH:39]=2)[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]=1)[CH3:9])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 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 59127148HCID 59127148, compoundYield 73.2%

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 (1.00 g, 2.47 mmol), methyl 6-chloronicotinate (0.450 g, 2.60 mmol), and cesium carbonate (1.204 g, 3.71 mmol) in acetonitrile (15 mL) was heated at 160° C. using microwave heating for 90 minutes. 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 isohexane, to give the desired compound (0.977 g).

Workup

  1. temperatureheating for 90 minutes
  2. customThe acetonitrile was removed in vaccuo
  3. customthe residual oil partitioned between water (50 mL) and ethyl acetate (75 mL)
  4. customThe ethyl acetate layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to a residue which
  8. customwas chromatographed on silica
  9. washeluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-ff05da9079964ac492f9cf4c244101ed
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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