Water → HCID 73426359, compound

HRID 1507594Notes

Reaction equation

HRID 1507594 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][C:23]=3[F:28])[CH:18]=2)[C:13]([CH3:31])([CH3:30])[C:12]1=[O:32])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[F:28][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:22]=1[C:21]([NH:20][C:17]1[CH:18]=[C:19]2[C:14]([C:13]([CH3:31])([CH3:30])[C:12](=[O:32])[N:11]2[CH2:10][CH2:9][OH:8])=[CH:15][CH:16]=1)=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 90046433HCID 90046433, compound

Product 1

HCID 73426359HCID 73426359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(1-(2-(tert-butyldimethylsilyloxy)ethyl)-3,3-dimethyl-2-oxoindolin-6-yl)-3-fluoroisonicotinamide (prepared in analogy to example 65c and 26 from 6-bromo-1-(2-(tert-butyldimethylsilyloxy)ethyl)-3,3-dimethylindolin-2-one and 3-fluoroisonicotinic acid; 195 mg, 426 μmol) in THF (10 ml) was added a solution of TBAF in THF (1M, 639 μl, 639 μmol). After 2 hours at room temperature the reaction mixture was treated with water and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel using dichloromethane/methanol (with 10% ammonia) as eluent. The title compound was obtained as light yellow solid (151 mg).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-420013d3498d406abf1b03699ca54643
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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