Tetrabutylammonium Fluoride → HCID 21091182, compound

HRID 351105Notes

Reaction equation

HRID 351105 reaction equation
C([Si](C)(C)[O:6][C:7]([C:10]1[NH:11][C:12]2[C:17]([C:18]=1[S:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1)=[CH:16][C:15]([C:29]#[N:30])=[C:14]([C:31]([F:34])([F:33])[F:32])[CH:13]=2)([CH3:9])[CH3:8])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][C:7]([C:10]1[NH:11][C:12]2[C:17]([C:18]=1[S:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1)=[CH:16][C:15]([C:29]#[N:30])=[C:14]([C:31]([F:33])([F:34])[F:32])[CH:13]=2)([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21091183HCID 21091183, compound

Product 1

HCID 21091182HCID 21091182, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-(3-nitro-phenylsulfanyl)-6-trifluoromethyl-1H-indole-5-carbonitrile (33 mg, 0.060 mmole) was stirred in THF (1 mL) with TBAF (1M in THF) (0.1 mL, 0.1 mmol). The reaction was allowed to proceed overnight and purified by column chromatography eluting with 0 and 1% methanol/dichloromethane. Obtained 17 mg (71%) of desired product. 1H NMR (acetone-d6) δ 11.75 (s, 1H), 8.19 (s, 1H), 8.08 (s, 1H), 7.98–7.96 (m, 1H), 7.81 (t, J=2.0 Hz, 1H), 7.54 (t. J=8.0 Hz, 1H), 7.48–7.45 (m, 1H), 2.83 (s, 1H), 1.75 (s, 6H). MS (m/z): 444 (MNa+), 420 (MH−).

Workup

  1. custompurified by column chromatography
  2. washeluting with 0 and 1% methanol/dichloromethane

Sources & evidence

ORD record
ord-13f4f9951098431bb558811662568700
Source dataset
uspto-grants-2007_02
Patent number
US07183309B2

Reaction notes

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