Sodium Carbonate → HCID 86699396, 화합물

HRID 1777564노트

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HRID 1777564 반응식
[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

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 18541883HCID 18541883, 화합물HCID 67974550HCID 67974550, 화합물

생성물 1

HCID 86699396HCID 86699396, 화합물수율 29%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-278fa5355e19465c995d4300161e1a13
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266832B2

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