Sodium Carbonate → Ethyl 6-phenylnicotinate

HRID 1177964

반응식

HRID 1177964 반응식
C([O-])([O-])=O.[Na+].[Na+].[CH2:7]([O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](Cl)=[N:13][CH:12]=1)[CH3:8].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.O.O.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>[CH2:7]([O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:13][CH:12]=1)[CH3:8]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 2799611Ethyl 6-chloronicotinate

생성물 1

HCID 11096332Ethyl 6-phenylnicotinate수율 64.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 22272177Toluene water용매

실험 절차

Na2CO3 (228 mg, 2.16 mmol) was added to a stirred solution of 6-chloro nicotinic acid ethyl ester (200 mg, 1.08 mmol) in toluene:H2O (5:1, 6 mL). Pd (PPh3)4 (250 mg, 0.216 mmol) and phenylboronic acid (168 mg, 1.29 mmol) were then added and the reaction mixture was heated to reflux for 3 hrs. The reaction mixture was then diluted with water and the product was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated to afford 140 mg (64.4% yield) of 6-phenyl-nicotinic acid ethyl ester. LCMS Purity %: 98.2

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hrs
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-53068b10f6614354a6f2ed2f028860e8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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