Tetrabutylammonium Fluoride → HCID 60026375, compound

HRID 400672Notes

Reaction equation

HRID 400672 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:25][C:26]([OH:45])([CH2:31][C:32]([C:35]2[C:43]3[O:42][CH2:41][CH2:40][C:39]=3[CH:38]=[C:37]([F:44])[CH:36]=2)([CH3:34])[CH3:33])[C:27]([F:30])([F:29])[F:28])(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:30][C:27]([F:28])([F:29])[C:26]([CH2:25][C:11]1[NH:10][C:18]2[C:13]([CH:12]=1)=[CH:14][C:15]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:17]=2)([OH:45])[CH2:31][C:32]([C:35]1[C:43]2[O:42][CH2:41][CH2:40][C:39]=2[CH:38]=[C:37]([F:44])[CH:36]=1)([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 60026513HCID 60026513, compound

Product 1

HCID 60026375HCID 60026375, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of the above 2-(1-benzenesulfonyl-5-pyridin-3-yl-1H-indol-2-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-4-methylpentan-2-ol (71 mg, 0.11 mmol) in 5 mL of THF was added a I M solution of tetrabutylammonium fluoride (0.5 mL, 0.5 mmol) in THF and the mixture was warmed at 80° C. After 18 hours, the mixture was concentrated in vacuo and diluted with 1 N aqueous sodium hydroxide solution and extracted with three 5 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of 1 N aqueous sodium hydroxide solution, 5 mL of brine, three 5 mL portions of saturated aqueous ammonium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified on silica gel eluting with methanol-dichloromethane (0:100, then 0.5:99.5, then 1:99) to afford 46 mg (83% yield) of the title compound.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with 1 N aqueous sodium hydroxide solution
  3. extractionextracted with three 5 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with two 5 mL portions of 1 N aqueous sodium hydroxide solution, 5 mL of brine, three 5 mL portions of saturated aqueous ammonium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on silica gel eluting with methanol-dichloromethane (0:100

Sources & evidence

ORD record
ord-19b6671396e64c048b9a6851959a5aad
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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