Sodium Carbonate → Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

HRID 1392618ノート

反応式

HRID 1392618 の反応式
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([Cl:11])=[CH:9][C:8](Cl)=[N:7][C:6]=1[CH3:13])[CH3:2].[CH2:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH3:24])[C:18]=1B(O)O)[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:18]2[C:19]([CH2:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:15][CH3:16])=[N:7][C:6]=1[CH3:13])[CH3:2]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2786748Ethyl 4,6-dichloro-2-methylnicotinateHCID 18437832(2,6-Diethylphenyl)boronic acid

生成物 1

HCID 59678345Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

A mixture of 4,6-dichloro-2-methyl-nicotinic acid ethyl ester (1.2 g, 5.1 mmol), 2,6-diethyl-phenyl boronic acid (2.18 g, 12.2 mmol), sodium carbonate (2 M aqueous solution, 12.2 mL, 24.4 mmol), and Pd(PPh3)4 (284 mg, 0.26 mmol) is refluxed in toluene for 48 hours and then cooled to room temperature. The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×50 mL). The organic layers are combined, dried, and solvent removed. The crude product is purified by flash column (hexanes/ethyl acetate 8:1) to give 4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester. 1H NMR: (CDCl3) 7.26 (t, 1H), 7.18 (s, 1H), 7.13 (d, 2H), 4.47 (q, 2H), 2.62 (s, 3H), 2.28 (q, 4H), 1.44 (t, 3H), 1.04 (t, 6H).

後処理

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with ethyl acetate (2×50 mL)
  3. customdried
  4. customsolvent removed
  5. customThe crude product is purified by flash column (hexanes/ethyl acetate 8:1)

出典と根拠

ORDレコード
ord-481bfc8fd0424b5b951ec98558ee2f66
出典データセット
uspto-grants-2008_03
特許番号
US07342115B2

反応ノート

読み込み中…