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

HRID 1024405노트

반응식

HRID 1024405 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.BrC1C2C(=NC=CC=2)N(S(C2C=CC(C)=CC=2)(=O)=O)C=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>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 3

HCID 2724141Tetrabutylammonium FluorideHCID 216691553-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 57774343HCID 57774343, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Compound 41 (4.37 g, 0.0164 mol) was dissolved in THE Molecular sieve (10 g of 3 A) 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. additionwas added
  2. washwashed several times with water, brine
  3. customthe organic layer was dried
  4. concentrationconcentrated in vacuo to an oil that

출처 및 근거

ORD 기록
ord-1945b721a12e4f758781a18680181923
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722889B2

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