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

HRID 1024405ノート

反応式

HRID 1024405 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1945b721a12e4f758781a18680181923
出典データセット
uspto-grants-2014_05
特許番号
US08722889B2

反応ノート

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