Water → HCID 21867506, compound

HRID 857328Notes

Reaction equation

HRID 857328 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[C:5]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:6][N:7]([Si](C(C)C)(C(C)C)C(C)C)[C:8]=2[CH:9]=[CH:10][CH:11]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH3:1][S:2][C:3]1[C:4]2[C:5]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)=[CH:6][NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 21867552HCID 21867552, compound

Product 1

HCID 21867506HCID 21867506, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the indole of Step 5 (1.9 g, 4.3 mmol) in THF (20 ml at 0° C. was added 1M TBAF (7 mL, 6 mmol). The reaction mixture was stirred for 1 minutes at 0° C. and water was added. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were dried over MgSO and concentrated The residue was purified by silica gel chromatography eluted with 20% EtOAc in Hexanes to provide 700 mg of the title compound as a pale yellow oil.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with Et2O
  3. dry with materialThe combined organic layers were dried over MgSO
  4. concentrationconcentrated The residue
  5. customwas purified by silica gel chromatography
  6. washeluted with 20% EtOAc in Hexanes

Sources & evidence

ORD record
ord-ec4a81e7275540e0867cb496d0cf88fc
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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