Sodium Carbonate → 5-phenyl-N-(2-(piperidin-1-yl)phenyl)furan-2-carboxamide

HRID 33471

반응식

HRID 33471 반응식
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([C:16]2[O:17][C:18](Br)=[CH:19][CH:20]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([C:16]2[O:17][C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 8891325-bromo-N-(2-piperidin-1-ylphenyl)furan-2-carboxamide

생성물 1

HCID 444445855-phenyl-N-(2-(piperidin-1-yl)phenyl)furan-2-carboxamide수율 75%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
80 °C

실험 절차

5-Bromo-furan-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide (1.0 mmol), phenylboronic acid (1.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) [“Pd(dppf)2Cl2”] (Aldrich) (0.05 mmol) and Na2CO3 (3.0 mmol) were dissolved in a solution of THF/H2O (4:1, 5 mL; saturated with argon) and heated to 80° C. for 5 h. After cooling to room temperature, the mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography to afford the pure product. Yield: 75%. MS: 347 (M+1). 1H NMR (CDCl3, 300 MHz): δ 9.90 (br s, 1H), 8.50 (d, 1H), 7.82 (d, 2H), 7.50-7.28 (m, 4H), 7.24-7.05 (m, 3H), 6.82 (d, 1H), 3.00-2.80 (m, 4H), 1.95-1.80 (m, 4H), 1.75-1.60 (m, 2H).

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel chromatography
  4. customto afford the pure product

출처 및 근거

ORD 기록
ord-e5bc71c734be4107ac09c9ea0e3c725e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429603B2

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