Sodium Carbonate → HCID 86699396、化合物

HRID 1777564ノート

反応式

HRID 1777564 の反応式
[F:1][C:2]1[C:3](I)=[C:4]([CH:6]=[C:7]([F:10])[C:8]=1[F:9])[NH2:5].[F:12][C:13]1[CH:14]=[C:15]([CH:37]=[CH:38][CH:39]=1)[CH2:16][C:17]1[CH:36]=[CH:35][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]#[C:27][Si:28]([CH2:33][CH3:34])([CH2:31][CH3:32])[CH2:29][CH3:30])=[O:22])=[CH:19][CH:18]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]([CH:37]=[CH:38][CH:39]=1)[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]2[C:3]3[C:4](=[CH:6][C:7]([F:10])=[C:8]([F:9])[C:2]=3[F:1])[NH:5][C:27]=2[Si:28]([CH2:29][CH3:30])([CH2:31][CH3:32])[CH2:33][CH3:34])=[O:22])=[CH:35][CH:36]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 18541883HCID 18541883、化合物HCID 67974550HCID 67974550、化合物

生成物 1

HCID 86699396HCID 86699396、化合物収率 29%

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

3,4,5-Trifluoro-2-iodoaniline (0.100 g; 0.366 mmol), 4-(3-fluorobenzyl)-N-(4-(triethylsilyl)but-3-ynyl)benzamide (0.145 g; 0.366 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.015 g; 0.018 mmol), lithium chloride (0.015 mg; 0.366 mmol) and sodium carbonate (0.078 g; 0.732 mmol) were suspended in DMF (5 mL) and the mixture was stirred at 100° C. for 72 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane) to afford 0.057 g (29%) of the title compound.

後処理

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted in ethyl acetate
  3. washThe organic layer was successively washed with brine, sodium thiosulfate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-278fa5355e19465c995d4300161e1a13
出典データセット
uspto-grants-2016_02
特許番号
US09266832B2

反応ノート

読み込み中…