Potassium Carbonate → Methyl 2-(4-chlorophenyl)nicotinate

HRID 1058318노트

반응식

HRID 1058318 반응식
Br[C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[N:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 12349191Methyl 2-bromopyridine-3-carboxylate

생성물 1

HCID 15318002Methyl 2-(4-chlorophenyl)nicotinate수율 93.5%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 1140Toluene용매

실험 절차

To a solution of methyl 2-bromonicotinate (5.6 g, 25.9 mmol) in toluene (140 mL) was added 4-chlorophenylboronic acid (6.1 g, 38.9 mmol), potassium carbonate (5.4 g, 39 mmol), and tetrakis(triphenylphosphine) palladium (1.53 g. 1.3 mmol). The mixture was heated to reflux for 3.5 hours, evaporated in vacuo and then purified on a silica gel column using a 1:4 mixture of ethyl acetate:hexane as mobile phase. Pure fractions were combined and the solvent was removed in vacuo to yield methyl 2-(4-chlorophenyl)nicotinate (6.0 g, HPLC RT=3.04 min, method A; LC-MS m/z=248).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. customevaporated in vacuo
  4. custompurified on a silica gel column
  5. additiona 1:4 mixture of ethyl acetate
  6. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-19fd726250af49daa1609b2c45afad92
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515011B2

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