Ethyl Propionate → 5-bromo-1-(toluene-4-sulfonyl)-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester

HRID 74465

반응식

HRID 74465 반응식
C(N(CC)C(C)C)(C)C.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:11][CH3:12].[Br:17][C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][C:21]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[C:20](I)[CH:19]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br-].[Zn+2].[Br-].O1CCCC1>[CH2:15]([O:14][C:10]([C:11]1[N:28]([S:29]([C:32]2[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=2)(=[O:31])=[O:30])[C:21]2[C:20]([CH:12]=1)=[CH:19][C:18]([Br:17])=[C:23]([C:24]([F:27])([F:25])[F:26])[CH:22]=2)=[O:13])[CH3:16]

참가 물질

7

반응물 3

HCID 7749Ethyl PropionateHCID 81531DiisopropylethylamineHCID 68005027N-(4-bromo-2-iodo-5-trifluoromethyl-phenyl)-4-methyl-benzenesulfonamide

생성물 1

HCID 680047005-bromo-1-(toluene-4-sulfonyl)-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester

시약·촉매·용매 3

HCID 10421208Zinc bromide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

N,N-diisopropylethyl amine (0.42 ml, 2.4 mmol), ethyl propionate (0.12 ml, 1.2 mmol), and tetrakis(triphenylphosphine)palladium (46 mg, 0.04 mmol) were added to an anhydrous tetrahydrofuran (THF) solution (3.2 ml) containing N-(4-bromo-2-iodo-5-trifluoromethyl-phenyl)-4-methyl-benzenesulfonamide (208 mg, 0.4 mmol) and zinc bromide (270 mg, 1.2 mmol). Then, the mixture was evacuated, and backfilled with argon. This was stirred at 80° C. for 13 hours. After cooling it to room temperature, the reaction mixture was filtered through Celite, and washed with ethyl acetate. The wash solution was washed with an aqueous solution saturated with sodium bicarbonate and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography. Thus, 5-bromo-1-(toluene-4-sulfonyl)-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester was obtained as a pale brown solid (195 mg, 50%).

후처리

  1. customThen, the mixture was evacuated
  2. temperatureAfter cooling it to room temperature
  3. filtrationthe reaction mixture was filtered through Celite
  4. washwashed with ethyl acetate
  5. washThe wash solution was washed with an aqueous solution saturated with sodium bicarbonate
  6. dry with materialan aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate
  7. customThe desiccant was removed by filtration, and concentration
  8. customThen, the residue obtained by concentration under reduced pressure
  9. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bd000ac9664b45088171998e60399da1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829199B2

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