Water → HCID 178452321, compound

HRID 1749901Notes

Reaction equation

HRID 1749901 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:32]=[CH:31][C:8]2[C:9](=[O:30])/[C:10](=[CH:12]/[C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15](COCC[Si](C)(C)C)[N:14]=3)/[O:11][C:7]=2[C:6]=1[CH2:33][N:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[NH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](/[CH:12]=[C:10]2\[O:11][C:7]3[C:6]([CH2:33][N:34]4[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:44])[CH3:45])=[O:41])[CH2:36][CH2:35]4)=[C:5]([O:4][CH2:3][CH2:2][OH:1])[CH:32]=[CH:31][C:8]=3[C:9]\2=[O:30])=[N:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86682033HCID 86682033, compound

Product 1

HCID 178452321HCID 178452321, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl (Z)-4-{[6-(2-hydroxyethoxy)-3-oxo-2-[(N-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl]methyl}piperazine-1-carboxylate (0.100 g, 0.154 mmol) obtained in Step 3 in THF (1 mL) was added with a 1 M solution of tetrabutylammonium fluoride in THF (1.54 mL, 1.54 mmol), and the mixture was refluxed for 3 hours by heating. The reaction mixture was cooled to room temperature, and then added with water (20 mL), the mixture was extracted three times with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over magnesium sulfate, and concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-6-(2-hydroxyethoxy)-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0440 g, 54%).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureby heating
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-2000f2c6b3e047488f44c1f13edec8f7
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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