Potassium Carbonate → 1-Acetyl-6-bromo-5-difluoromethoxyindoline

HRID 3022

반응식

HRID 3022 반응식
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl[C:16]([F:22])([F:21])C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH:16]([F:22])[F:21])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 73935Methyl chlorodifluoroacetate2회HCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one

생성물 1

HCID 196887861-Acetyl-6-bromo-5-difluoromethoxyindoline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-Acetyl-6-bromo-5-hydroxyindoline (2 g, 7.8 mmol), methyl 2-chloro-2,2-difluoroacetate (0.82 ml, 7.8 mmol) and potassium carbonate (1.08 g, 7.8 mmol) were suspended in N,N-dimethylformamide (20 mL) under an argon atmosphere and placed in a 65° C. oil bath. After 3 hr, additional methyl 2-chloro-2,2-difluoroacetate (0.3 ml, 2.8 mmol) and potassium carbonate (0.3 g, 2.2 mmol) was added and heated for 18 hr. The solvent was then removed in vacuo and the residue was partitioned between cold 3N HCl and ether. The aqueous layer was extracted three times with ether, the combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated. The solid was purified by flash chromatography (2% MeOH/CH2Cl2) to provide the title compound as a white solid

후처리

  1. customplaced in a 65° C.
  2. temperatureheated for 18 hr
  3. customThe solvent was then removed in vacuo
  4. customthe residue was partitioned between cold 3N HCl and ether
  5. extractionThe aqueous layer was extracted three times with ether
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid was purified by flash chromatography (2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-550474a9556d462983b860f2b003f86a
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731477

연결된 노트

불러오는 중…