Sodium Carbonate → HCID 58641236、化合物

HRID 1594443ノート

反応式

HRID 1594443 の反応式
[C:1]1([C@@H:7]2[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH2:9][N:8]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[F:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[C:10]1[CH2:9][N:8]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 59682332HCID 59682332、化合物

生成物 1

HCID 58641236HCID 58641236、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A deoxygenated mixture of crude tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate (2-4, 7.65 mmol), 2,5-difluorophenyl boronic acid (1.81 g, 11.5 mmol), aqueous Na2CO3 solution (2 M, 11.5 mL, 23.0 mmol), and Pd(PPh3)4 (0.442 g, 0.383 mmol) in dioxane (100 mL) was heated at 90° C. for 45 minutes. The reaction mixture was cooled, then partitioned between brine (200 mL) and a 1:1 mixture of ethyl acetate and hexane (200 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (SiO2, O-50% EtOAc/hexanes gradient) to provide tert-butyl (2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (2-5) as a white solid. LRMS nvz (M+H-CH3) 358.0 found, 358.2 required.

後処理

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between brine (200 mL)
  3. additiona 1:1 mixture of ethyl acetate and hexane (200 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (SiO2

出典と根拠

ORDレコード
ord-73c240a8196848df9f594a2b292a645b
出典データセット
uspto-grants-2007_11
特許番号
US07301028B2

反応ノート

読み込み中…