Cesium carbonate → 4-((3-(difluoromethoxy)-2-methoxy-6-(1-oxo-2,3-dihydro-1H-inden-4-yl)phenoxy)methyl)benzamide

HRID 2171078노트

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HRID 2171078 반응식
Br[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][CH:11]=2)=[C:6]([O:19][CH3:20])[C:5]([O:21][CH:22]([F:24])[F:23])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:39]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:40]=2[CH2:41][CH2:42][C:43]3=[O:48])O1>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:23][CH:22]([F:24])[O:21][C:5]1[C:6]([O:19][CH3:20])=[C:7]([C:2]([C:39]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:40]=2[CH2:41][CH2:42][C:43]3=[O:48])=[CH:3][CH:4]=1)[O:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-oneHCID 674639064-((6-Bromo-3-(difluoromethoxy)-2-methoxyphenoxy)methyl)benzamide

생성물 1

HCID 674680644-((3-(difluoromethoxy)-2-methoxy-6-(1-oxo-2,3-dihydro-1H-inden-4-yl)phenoxy)methyl)benzamide수율 26.7%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A stirring solution of 4-((6-bromo-3-(difluoromethoxy)-2-methoxyphenoxy)methyl)benzamide (500 mg, 1.24 mmol) in dimethylformamide (10 mL) was purged with argon for 1 h, to this cesium carbonate (1.2 g, 3.73 mmol), tetrakis(triphenylphosphine) palladium(0) (72 mg, 0.06 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (641 mg, 2.48 mmol) was added and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT and filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 0-80% ethyl acetate in pet ether) to afford title compound as a solid (150 mg, 26.7%).

후처리

  1. additionwas added
  2. customthe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, 0-80% ethyl acetate in pet ether)

출처 및 근거

ORD 기록
ord-e16d07b40ae14a33b4ce8d496ec602cf
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051290B2

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