Tetrabutylammonium Fluoride → 3-(2-tert-butylphenyl)-1H-indole

HRID 2423218Notes

Reaction equation

HRID 2423218 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13](S(C2C=CC=CC=2)(=O)=O)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 672419373-(2-tert-butylphenyl)-1-(phenylsulfonyl)-1H-indole

Product 1

HCID 672410893-(2-tert-butylphenyl)-1H-indoleYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

3-(2-tert-Butylphenyl)-1-(phenylsulfonyl)-1H-indole (172.6 mg, 0.443 mmol) was combined with tetrahydrofuran (2.0 mL) and 1 M tetrabutylammonium fluoride solution (2.21 mL) and heated to 100° C. for 20 minutes. The cooled reaction is charged to a silica gel column and purified by eluting with a gradient of ethyl acetate and hexanes to give 3-(2-tert-butylphenyl)-1H-indole (26.8 mg, 26%) as a colorless solid.

Workup

  1. customThe cooled reaction
  2. additionis charged to a silica gel column
  3. custompurified
  4. washby eluting with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-9477f39a4a7f45c9bc00c6c2ee272aaa
Source dataset
uspto-grants-2011_06
Patent number
US07960569B2

Reaction notes

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