Tetrabutylammonium Fluoride → 5-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1786764Notes

Reaction equation

HRID 1786764 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([Si](CC)(CC)CC)[NH:8][C:5]2=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57774343HCID 57774343, compound

Product 1

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 41 (4.37 g, 0.0164 mol) was dissolved in THF. Molecular sieve (10 g of 3A) was added followed by TBAF (32.75 mL, 0.0328). The reaction mixture was stirred for 5 h at rt. Diluted with ethyl acetate and washed several times with water, brine and the organic layer was dried and concentrated in vacuo to an oil that was subjected to flash chromatography (30% EtOAc-70% hexanes) to give 02.3 g (90%) of the desired material 42. 1H NMR DMSO d6 11.8 (bs, 1H), 8.2 (s, 1H), 8.1 (s, 1H), 7.5 (s, 1H), 6.5 (s, 1H).

Workup

  1. washwashed several times with water, brine
  2. customthe organic layer was dried
  3. concentrationconcentrated in vacuo to an oil that

Sources & evidence

ORD record
ord-3a668e086f9d4af2aefd449954e6ab0e
Source dataset
uspto-grants-2009_03
Patent number
US07507826B2

Reaction notes

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