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

HRID 1481172ノート

反応式

HRID 1481172 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-d705a3f60edf48d1b4ebb19b4a5af32d
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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