Sodium Carbonate → N-cyclopropyl-3-(4,4-diethoxybutyl)-4-fluorobenzamide

HRID 6872

반응식

HRID 6872 반응식
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH:6]=[CH2:7])[CH3:2].B1C2CCCC1CCC2.C([O-])([O-])=O.[Na+].[Na+].Br[C:27]1[CH:28]=[C:29]([CH:36]=[CH:37][C:38]=1[F:39])[C:30]([NH:32][CH:33]1[CH2:35][CH2:34]1)=[O:31]>C(OCC)(=O)C.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.CCO.C1C=CC=CC=1>[CH:33]1([NH:32][C:30](=[O:31])[C:29]2[CH:36]=[CH:37][C:38]([F:39])=[C:27]([CH2:7][CH2:6][CH2:5][CH:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2])[CH:28]=2)[CH2:34][CH2:35]1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 2564264,4-Diethoxybut-1-eneHCID 220190903-Bromo-N-cyclopropyl-4-fluorobenzamide

생성물 1

HCID 22019163N-cyclopropyl-3-(4,4-diethoxybutyl)-4-fluorobenzamide수율 93.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A solution of 3-butenal diethyl acetal (144 mg, 1 mmol) and 9-BBN (0.5 M in THF, 2.2 mL, 1.1 mmol) was stirred at RT for 1 h. The mixture was concentrated and to the residue were added benzene (2 mL), EtOH (1 mL), aqueous Na2CO3 solution (2M, 1 mL), 3-bromo-4-fluoro-N-cyclopropylbenzamide (127 mg, 0.5 mmol) and Pd(Ph3P)4 (40 mg). The resulting mixture was stirred at 80° C. for 2 h. The mixture was then cooled to RT and diluted with ethyl acetate (10 mL) and washed with water. The organic layer was separated and concentrated. The residue was purified by column chromatography (SiO2; EtOAc/hexane 1:3) to afford N-cyclopropyl-3-(4,4-diethoxybutyl)-4-fluorobenzamide (151 mg, 93%). This material was dissolved in acetone (1 mL) and 3 N HCl solution (0.2 mL) and stirred at RT for 1 h. The mixture was neutralized with NaHCO3 solution and extracted with ethyl acetate (3×5 mL). The organic layer was dried and concentrated to afford N-cyclopropyl-4-fluoro-3-(4-oxo-butyl)-benzamide (110 mg, 94%).

후처리

  1. concentrationThe mixture was concentrated and to the residue
  2. temperatureThe mixture was then cooled to RT
  3. washwashed with water
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2; EtOAc/hexane 1:3)

출처 및 근거

ORD 기록
ord-b66a4138f5a24ea6bea939d006b10a7b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084160B2

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