Sodium t-butoxide → N-[5-[3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl]indan-1-yl]propanamide

HRID 1500191

反応式

HRID 1500191 の反応式
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:13]2([C:18]([F:21])([F:20])[F:19])[CH2:17][CH2:16][NH:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[CH:30]([NH:34][C:35](=[O:38])[CH2:36][CH3:37])[CH2:29][CH2:28]2.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2([C:18]([F:21])([F:19])[F:20])[CH2:17][CH2:16][N:15]([C:25]3[CH:26]=[C:27]4[C:31](=[CH:32][CH:33]=3)[CH:30]([NH:34][C:35](=[O:38])[CH2:36][CH3:37])[CH2:29][CH2:28]4)[CH2:14]2)[CH:4]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:8]=1

参加物

8

反応物 3

HCID 23676156Sodium t-butoxideHCID 532621863-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidineHCID 59453384N-(5-bromoindan-1-yl)propionic acid amide

生成物 1

HCID 45377922N-[5-[3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl]indan-1-yl]propanamide収率 72.6%

試薬・触媒・溶媒 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidine (0.46 g) and N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propanamide (0.35 g) were dissolved in toluene and deaeration procedure was performed three times under argon atmosphere. Sodium tert-butoxide (0.25 g), Xantphos (0.05 g) and tris(dibenzylideneacetone)dipalladium (0) (chloroform adduct) (0.03 g) were added to the mixture and heated and stirred at 100° C. under argon atmosphere for 2 hours. The solution was cooled to room temperature and the reaction liquid was diluted with ethyl acetate followed by washing with water and brine. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered and separated, the solvent was evaporated off under reduced pressure, and the residue was purified by a silica gel chromatography to obtain N-(5-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoro-methyl)pyrrolidin-1-yl}-2,3-dihydro-1H- -inden-1-yl)propanamide (0.51 g).

後処理

  1. temperatureheated
  2. temperatureThe solution was cooled to room temperature
  3. customthe reaction liquid
  4. washby washing with water and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered
  7. customseparated
  8. customthe solvent was evaporated off under reduced pressure
  9. customthe residue was purified by a silica gel chromatography

出典と根拠

ORDレコード
ord-0f571116a842404e97ff515c87c9012d
出典データセット
uspto-grants-2015_12
特許番号
US09206122B2

関連ノート

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