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

HRID 1481172노트

반응식

HRID 1481172 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d705a3f60edf48d1b4ebb19b4a5af32d
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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