Tetrabutylammonium Fluoride → HCID 46183927, compound

HRID 341303Notes

Reaction equation

HRID 341303 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[C:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:17]=3)[C:12]3[CH:27]=[C:28]([Cl:31])[CH:29]=[N:30][C:11]2=3)(=O)=O)C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:31][C:28]1[CH:29]=[N:30][C:11]2[NH:10][C:18]3[C:13]([C:12]=2[CH:27]=1)=[CH:14][C:15]([C:19]#[C:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:16][CH:17]=3

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 46183926HCID 46183926, compound

Product 1

HCID 46183927HCID 46183927, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9-benzenesulfonyl-3-chloro-6-(2-phenylethynyl)-9H-pyrido[2,3-b]indole (88 mg, 0.20 mmol, 1 equiv.) in anhydrous THF under argon, TBAF 1M in THF (1 ml, 1 mmol, 5 equiv.) is added dropwise. The reaction is carried out at reflux for 4 hours and then evaporated. The crude product (yellow solid) is purified over silica gel chromatography (CH2Cl2/AcOEt 9:1) to afford the product 60 as a white solid (53 mg, 0.18 mmol) in 88% yield. 1H NMR (300 MHz, DMSO d6) δ 12.25 (br s, 1H), 8.77 (d, 1H, J=2.5 Hz), 8.49 (br s, 1H), 8.47 (d, 1H, J=2.5 Hz), 7.67 (dd, 1H, J=1.5, 8.5 Hz), 7.59-7.54 (m, 3H), 7.45-7.42 (m, 3H).

Workup

  1. temperatureat reflux for 4 hours
  2. customevaporated
  3. customThe crude product (yellow solid) is purified over silica gel chromatography (CH2Cl2/AcOEt 9:1)

Sources & evidence

ORD record
ord-2a85340810234d21b501a38661866c85
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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