C16H22F6IN2P → Ethyl 7-bromo-4-hydroxy-1-iodo-3-isoquinolinecarboxylate

HRID 1481167ノート

反応式

HRID 1481167 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([Br:17])[CH:10]=2)=[O:5])[CH3:2].CC1C=C(C)N=C(C)C=1.CC1C([IH+:34])=C(C)N=C(C)C=1.F[P-](F)(F)(F)(F)F>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([I:34])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([Br:17])[CH:10]=2)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 46863890C16H22F6IN2PHCID 89813095Ethyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

生成物 1

HCID 89812910Ethyl 7-bromo-4-hydroxy-1-iodo-3-isoquinolinecarboxylate収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

7-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (1.0 g, 3.37 mmol) was dissolved in dry dichloromethane (30 mL) and bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate (3.5 g, 6.754 mmol) was added in one portion as a solid. The solution was protected from light and permitted to stir overnight at room temperature. Upon completion, the reaction was quenched by addition of aqueous sodium thiosulfate (2.0 g in 50 mL of water. The layers were separated and the organic phase washed with 1M hydrochloric acid, brine and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography (3-15% ethyl acetate in hexanes) to provide the iodo-isoquinoline in 77% yield which was used immediately in the next step.

後処理

  1. customUpon completion, the reaction was quenched by addition of aqueous sodium thiosulfate (2.0 g in 50 mL of water
  2. customThe layers were separated
  3. washthe organic phase washed with 1M hydrochloric acid, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude material was purified by silica gel chromatography (3-15% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-a6c9a8e1cd2045f4abd56edcff105214
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

読み込み中…