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

HRID 33540

反応式

HRID 33540 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 20099850Methyl 5-(3-chlorophenyl)nicotinate収率 80.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-48cf15a1bb314f92a712ee4b2305e794
出典データセット
uspto-grants-2008_09
特許番号
US07429605B2

関連ノート

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