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

HRID 1786764노트

반응식

HRID 1786764 반응식
[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

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 57774343HCID 57774343, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3a668e086f9d4af2aefd449954e6ab0e
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507826B2

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