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

HRID 251597노트

반응식

HRID 251597 반응식
[CH3:1][O:2][C:3](=[O:21])[C:4]1[C:9](Cl)=[CH:8][C:7]([C:11]2[C:16]([CH2:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:19][CH3:20])=[N:6][CH:5]=1.B(CC)(CC)[CH2:23][CH3:24].C([O-])([O-])=O.[Na+].[Na+].CCCCCC>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>[CH3:1][O:2][C:3](=[O:21])[C:4]1[C:9]([CH2:23][CH3:24])=[CH:8][C:7]([C:11]2[C:16]([CH2:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:19][CH3:20])=[N:6][CH:5]=1

참가 물질

7

반응물 4

HCID 7357TriethylboraneHCID 8058HexaneHCID 10340Sodium CarbonateHCID 596781594-Chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester

생성물 1

HCID 596783286-(2,6-Diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester (2.5 g, 8.2 mmol), Et3B (1M in Hexane, 49 mL, 49 mmol), Na2CO3 (2M in H2O, 12.3 mL) and Pd(PPh3)4 (500 mg) in toluene (36 mL) is heated at 80° C. under argon for 2 days. On cooling, hexane (50 mL) is added and the organic layer separated. The organic layer is washed with saturated Na2CO3 and water, dried (Na2SO4), and concentrated. The residue is purified by silica gel chromatography (hexane/EtOAc 4:1) to give 6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester. 1H NMR (CDCl3) 9.15 (s, 1H), 7.30 (m, 1H), 7.21 (s, 1H), 7.15 (d, 2H), 3.97 (s, 3H), 3.06 (q, 2H), 2.31 (m, 4H), 1.26 (t, 3H), 1.03 (t, 6H).

후처리

  1. temperatureOn cooling
  2. customthe organic layer separated
  3. washThe organic layer is washed with saturated Na2CO3 and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography (hexane/EtOAc 4:1)

출처 및 근거

ORD 기록
ord-011c08155e794e2e84183dc8ceec273d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863454B2

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