Ethyl Acetate → Methyl 6-(4-hydroxyphenyl)-2-pyridinecarboxylate

HRID 1717206ノート

反応式

HRID 1717206 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>O1CCOCC1.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>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 16217886Methyl 6-bromopyridine-2-carboxylate

生成物 1

HCID 136146660Methyl 6-(4-hydroxyphenyl)-2-pyridinecarboxylate収率 46%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of methyl 6-bromo-2-pyridinecarboxylate (1.35 g, 6.22 mmol, 1 eq), (4-hydroxyphenyl)boronic acid (0.945 g, 6.85 mmol, 1.1 eq), Pd(PPh3)4 (0.718 g, 0.06 mmoles, 0.01 eq) and K2CO3 (1.7 g, 12.4 mmoles, 2 eq) in dioxane (15 mL) and water (8 mL) was heated at 100° C. for 2 h. Then AcOEt was added and the organic phase was washed with water, dried over Na2SO4, filtered and evaporated to dryness. The crude compound was purified on flash chromatography on 50 g silica gel cartridge using a gradient of cyclohexane/ethyl acetate 10/0 to 7/3 as an eluent. Solvents were removed under reduced pressure to give the title compound as a yellow solid (650 mg, 46%). 1H-NMR (CDCl3, 400 MHz): δ 4.03 (3H, s), 5.28 (1H, s), 6.90-7.03 (2H, m), 7.80-7.98 (2H, m), 8.0-8.06 (3H, m). MS: (ES/+) m/z: 230 (M+H)+. C13H11NO3 requires 229.

後処理

  1. washthe organic phase was washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude compound was purified on flash chromatography on 50 g silica gel cartridge
  6. customSolvents were removed under reduced pressure

出典と根拠

ORDレコード
ord-f4577e340f5541558c3cdee59ae47a6e
出典データセット
uspto-grants-2010_09
特許番号
US07803833B2

反応ノート

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