Tetrabutylammonium Fluoride → HCID 59129336, compound

HRID 1908445Notes

Reaction equation

HRID 1908445 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 59129340HCID 59129340, compound

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%). 1H NMR (400 MHz, CDCl3) δ 8.56 (brs, 1H), 8.44 (d, J=2.0 Hz, 1H), 8.01 (dd, J=2.4, 8.8 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 6.34 (d, J=1.6 Hz, 1H), 1.52 (s, 3H), 1.03-0.97 (m, 2H), 0.89-0.83 (m, 2H).

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-0664fa0157664ae6921200e0675041f1
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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