Tetrabutylammonium Fluoride → HCID 21091182, compound

HRID 1393311Notes

Reaction equation

HRID 1393311 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 (1 M 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-8453f43c432d4609a194400081da8632
Source dataset
uspto-grants-2008_03
Patent number
US07345084B2

Reaction notes

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