Tetrabutylammonium Fluoride → 5-Fluoro-6-(4-methoxy-benzenesulfonyl)-3,3-dimethyl-2,3-dihydro-1H-indole

HRID 1475331Notes

Reaction equation

HRID 1475331 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[N:7]([Si](C(C)C)(C(C)C)C(C)C)[CH2:6][C:5]2([CH3:33])[CH3:32].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[NH:7][CH2:6][C:5]2([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867239505-Fluoro-6-(4-methoxy-benzenesulfonyl)-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole

Product 1

HCID 867239515-Fluoro-6-(4-methoxy-benzenesulfonyl)-3,3-dimethyl-2,3-dihydro-1H-indoleYield 64.3%

Procedure

5-Fluoro-6-(4-methoxy-benzenesulfonyl)-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole (250 mg, 0.51 mmol) was treated with TBAF following similar methods to those described in Preparation 78 to give the title compound (110 mg) as a pale yellow oil. 1H NMR (CDCl3): 7.99-7.81 (2H, m), 7.21 (1H, d), 7.04-6.92 (2H, m), 6.73 (1H, d), 3.87 (3H, s), 3.35 (2H, s), 1.27 (6H, s).

Workup

  1. customthose described in Preparation 78

Sources & evidence

ORD record
ord-fd0d82758c5c4dfc8d167f992c7e94c4
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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