Potassium Carbonate → tert-butyl 1-(3-(4-chlorophenyl)-5,5,5-trifluoropent-1-yn-3-yl)-1H-indazol-4-ylcarbamate

HRID 1477905Notes

Reaction equation

HRID 1477905 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH2:11][C:12]([F:15])([F:14])[F:13])[CH:9]=O)=[CH:4][CH:3]=1.[C:33]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:31])[CH3:29])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH2:11][C:12]([F:13])([F:14])[F:15])[C:9]#[CH:33])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86705054tert-butyl 1-(2-(4-chlorophenyl)-4,4,4-trifluoro-1-oxobutan-2-yl)-1H-indazol-4-ylcarbamateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86705055tert-butyl 1-(3-(4-chlorophenyl)-5,5,5-trifluoropent-1-yn-3-yl)-1H-indazol-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step C (120 mg, 0.25 mmol) in methanol (5 mL) was added K2CO3 (69 mg, 0.5 mmol), dimethyl 1-diazo-2-oxopropylphosphonate (96 mg, 0.5 mmol). The mixture was stirred at room temperature for 2 h. After removing the organic solvent, the residue was added H2O (10 mL), extracted with ethyl acetate, and washed with brine (10 mL), dried over sodium sulfate, then filtered. The organic solvent was evaporated, and the residue was purified by silica gel chromatography (EA/PE=1:8) to obtain the title compound as colorless oil. LC/MS m/z=464.1[M+H]+.

Workup

  1. customAfter removing the organic solvent
  2. additionthe residue was added H2O (10 mL)
  3. extractionextracted with ethyl acetate
  4. washwashed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe organic solvent was evaporated
  8. customthe residue was purified by silica gel chromatography (EA/PE=1:8)

Sources & evidence

ORD record
ord-a7131de167fb4aa68c1ae615c2d71af9
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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