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

HRID 1058318ノート

反応式

HRID 1058318 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 15318002Methyl 2-(4-chlorophenyl)nicotinate収率 93.5%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-19fd726250af49daa1609b2c45afad92
出典データセット
uspto-grants-2003_02
特許番号
US06515011B2

反応ノート

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