Sodium Methoxide → 6-[5-Fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboximidic acid methyl ester

HRID 340084Notes

Reaction equation

HRID 340084 reaction equation
[F:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]([CH2:25][C:26]([F:29])([F:28])[F:27])=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:23]#[N:24])=[N:13][N:14]3[CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:10][CH:9]=2)[CH:7]=1.[CH3:32][O-:33].[Na+]>CO>[CH3:32][O:33][C:23]([C:12]1[C:11]2[C:15](=[CH:16][C:8]([C:6]3[CH:7]=[C:2]([F:1])[C:3]([O:30][CH3:31])=[CH:4][C:5]=3[CH2:25][C:26]([F:29])([F:28])[F:27])=[CH:9][CH:10]=2)[N:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[N:13]=1)=[NH:24]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 712380616-[5-Fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbonitrile

Product 1

HCID 866762786-[5-Fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboximidic acid methyl esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-[5-fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbonitrile (Preparation 37, 1.737 g, 4.00 mmol) in methanol (40 mL) was added sodium methoxide (648 mg, 12.0 mmol) and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between EtOAc (50 mL) and water (50 mL) and the aqueous layer was extracted with further EtOAc (2×50 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the title compound as an oily solid (1.64 g) in an 88% yield.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (50 mL) and water (50 mL)
  2. extractionthe aqueous layer was extracted with further EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b997011fd4f84d6da10bb181c8e32313
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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