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

HRID 1786764ノート

反応式

HRID 1786764 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.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

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 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 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-3a668e086f9d4af2aefd449954e6ab0e
出典データセット
uspto-grants-2009_03
特許番号
US07507826B2

反応ノート

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