Water → methyl 3-(4-(2,3-dihydro-1H-inden-2-yloxy)-2-cyano-5-(1-methyl-1H-indazol-5-yl)phenyl)propanoate

HRID 1620028Notes

Reaction equation

HRID 1620028 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[C:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[N:21]=[CH:20]3)=[CH:15][C:14]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:13](OS(C(F)(F)F)(=O)=O)[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O.C(OCC)(=O)C.[CH3:54][N:55](C)C(=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[C:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[N:21]=[CH:20]3)=[CH:15][C:14]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:13]([C:54]#[N:55])[CH:12]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 86640868Methyl 3-(4-(2,3-dihydro-1H-inden-2-yloxy)-5-(1-methyl-1H-indazol-5-yl)-2-(trifluoromethylsulfonyloxy)phenyl)propanoate

Product 1

HCID 66877829methyl 3-(4-(2,3-dihydro-1H-inden-2-yloxy)-2-cyano-5-(1-methyl-1H-indazol-5-yl)phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
120 °C

Procedure

A solution of Intermediate 6 (30 mg) in N,N-dimethylacetamide (1 ml) was added with K4[Fe(CN)6]·3H2O (6.6 mg, Ald), sodium carbonate (5.5 mg), and palladium acetate (1.1 mg, WAKO), and stirred at 120° C. for 5 hours. The reaction mixture was added with water (3 ml), and ethyl acetate (3 ml×2) for extraction, and then successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine, the organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1), and the solvent was evaporated under reduced pressure by using a rotary evaporator to obtain the title compound (yield: 10 mg).

Workup

  1. washsuccessively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  2. customthe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)
  5. customthe solvent was evaporated under reduced pressure
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-4c36a953f23d4630965b234aadfc7ada
Source dataset
uspto-grants-2014_07
Patent number
US08772327B2

Reaction notes

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