Tetrabutylammonium Fluoride → HCID 59129336, compound

HRID 2037974Notes

Reaction equation

HRID 2037974 reaction equation
[CH3:1][C:2]1([C:5]#[C:6][C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[NH:16]C(=O)CCC)[CH2:4][CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][C:2]1([C:5]2[NH:16][C:8]3[C:7]([CH:6]=2)=[CH:12][C:11]([N+:13]([O-:15])=[O:14])=[CH:10][CH:9]=3)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59129340N-(2-(1-methyl-cyclopropylethynyl)-4-nitro-phenyl]-butyramide

Product 1

HCID 59129336HCID 59129336, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[2-(1-methyl-cyclopropylethynyl)-4-nitro-phenyl]-butyramide (1.3 g, 4.6 mmol) and TBAF (2.4 g, 9.2 mmol) in THF (20 mL) was heated at reflux for 24 h. The mixture was cooled to room temperature and poured into ice water. The mixture was extracted with CH2Cl2(30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to afford 2-(1-methylcyclopropyl)-5-nitro-1H-indole (0.70 g, 71%). 1 H NMR (400 MHz, CDCl3) δ 8.56(brs, 1 H), 8.44(d, J=2.0 Hz, 1 H), 8.01(dd, J=2.4, 8.8 Hz, 1 H), 7.30(d, J=8.8 Hz, 1 H), 6.34(d, J=1.6 Hz, 1 H), 1.52(s, 3 H), 1.03-0.97(m, 2 H), 0.89-0.83(m, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. extractionThe mixture was extracted with CH2Cl2(30 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-a6ca48e4e56047c9b12f6346ac55ae28
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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