Cesium carbonate → Methyl 5-(3-chlorophenyl)nicotinate

HRID 33540

반응식

HRID 33540 반응식
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:23][O:24][C:25]([C:27]1[CH:28]=[N:29][CH:30]=[C:31](Br)[CH:32]=1)=[O:26]>C(COC)OC.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>[CH3:23][O:24][C:25](=[O:26])[C:27]1[CH:32]=[C:31]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:30]=[N:29][CH:28]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 699336Methyl 5-bromopyridine-3-carboxylateHCID 100372252-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 20099850Methyl 5-(3-chlorophenyl)nicotinate수율 80.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

104 mg (0.09 mmol)Pd(PPh3)4, 1.5 g (6.29 mmol) of 3-chlorophenylboronic acid pinacol ester 2.86 ml (8.58 mmol) and 3M cesium carbonate solution were added under argon at room temperature to a solution of 1.24 g (5.72 mmol) methyl-5-bromo-pyridine-3-carboxylate in 45 ml dimethoxyethane and the mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and evaporated. The residue was taken up with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.14 g (72%) of 5-(3-Chloro-phenyl)-nicotinic acid methyl ester

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 min
  3. customevaporated
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

출처 및 근거

ORD 기록
ord-48cf15a1bb314f92a712ee4b2305e794
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429605B2

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