Triethylborane → 6-(2,6-Diethyl-phenyl)-4-ethyl-2-methyl-nicotinic acid ethyl ester

HRID 251622ノート

反応式

HRID 251622 の反応式
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10](Cl)=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])[CH3:2].[CH2:24](B(CC)CC)[CH3:25].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.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:23])[C:5]1[C:10]([CH2:24][CH3:25])=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])[CH3:2]

参加物

7

反応物 3

HCID 7357TriethylboraneHCID 10340Sodium CarbonateHCID 59678345Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

生成物 1

HCID 669936416-(2,6-Diethyl-phenyl)-4-ethyl-2-methyl-nicotinic acid ethyl ester収率 64.3%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

A mixture of 4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester (251 mg, 0.76 mmol), triethylborane (4.6 mL of 1 M solution in hexane, 4.6 mmol), Pd(PPh3)4 (26 mg, 0.023 mmol), and Na2CO3 (1.27 g, 6 mL of 2M solution in H2O) in toluene (20 mL) is heated for 48 hours at 95° C. After cooling to room temperature the mixture is diluted with water (10 mL) and extracted with EtOAc. The combined extracts are washed with saturated brine, dried (Na2SO4), concentrated, and purified by flash chromatography (elution with hexane/EtOAc 10:1) to yield 159 mg 6-(2,6-diethyl-phenyl)-4-ethyl-2-methyl-nicotinic acid ethyl ester as a colorless oil: 1H NMR (CDCl3) 7.29 (dd, 1H), 7.13 (d, 2H), 7.00 (s, 1H), 4.47 (q, 2H), 2.68 (q, 2H), 2.59 (s, 3H), 2.0-2.3.7 (m, 4H), 1.45 (t, 3H), 1.24 (t, 3H), 1.05 (t, 6H).

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with EtOAc
  3. washThe combined extracts are washed with saturated brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography (elution with hexane/EtOAc 10:1)

出典と根拠

ORDレコード
ord-841444e41b6e45f8bf17acfd30cf59c5
出典データセット
uspto-grants-2011_01
特許番号
US07863454B2

反応ノート

読み込み中…