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2-Fluoro-3-methoxyphenylboronic acid → 1-(2,6-Difluorobenzyl)-2,6-dimethyl-3-(2-fluoro-3-methoxyphenyl)-5-ethoxycarbonyl-4-pyridone

HRID 495522
ノート
印刷プレビュー

反応式

HRID 495522 の反応式
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][N:5]1[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:8](=[O:17])[C:7](Br)=[C:6]1[CH3:19].[F:25][C:26]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.[OH-].[Ba+2].[OH-]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1.C(O)C.COCCOC>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][N:5]1[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:8](=[O:17])[C:7]([C:27]2[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:26]=2[F:25])=[C:6]1[CH3:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 49857442-Fluoro-3-methoxyphenylboronic acidHCID 6093286Barium hydroxideHCID 223272271-(2,6-Difluorobenzyl)-2,6-dimethyl-3-bromo-5-ethoxycarbonyl-4-pyridone

生成物 1

HCID 223272391-(2,6-Difluorobenzyl)-2,6-dimethyl-3-(2-fluoro-3-methoxyphenyl)-5-ethoxycarbonyl-4-pyridone

試薬・触媒・溶媒 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 86588578Benzene ethanol 1,2-dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

1-(2,6-Difluorobenzyl)-2,6-dimethyl-3-bromo-5-ethoxycarbonyl-4-pyridone (1.5 g, 3.7 mmol) was evacuated in a pressure vessel with 2-fluoro-3-methoxyphenyl boronic acid (764 mg, 4.5 mmol) and tetrakis(triphenylphosphine) palladium (0) (428 mg, 370 μmol). A mixture of benzene/ethanol/1,2-dimethoxyethane (74 ml in a 10/1/11 ratio) and barium hydroxide (saturated aqueous, about 0.5M) was then added under vacuum, the vessel sealed under N2, and the reaction stirred at 90° C. for twelve hours, protected from light. The organic layer was concentrated and purified using flash silica chromatography (EtOAc/hexanes-1/4 to MeOH/CH2Cl2-2/98), with the product eluting as the third spot. The product was dried as an amber oil (1.12 g, 2.5 mmol, 68%). 1H NMR (CDCl3, 300 MHz) δ 6.80-7.80 (m, 6H), 5.29 (s, 2H), 4.37-4.33 (m, 2H), 3.87 (s, 3H), 3.38 (s, 3H), 2.26 (s, 3H), 1.35 (t, 3H); LCMS=446 (MH+).

後処理

  1. additionwas then added under vacuum
  2. customthe vessel sealed under N2
  3. concentrationThe organic layer was concentrated
  4. custompurified
  5. washwith the product eluting as the third spot

出典と根拠

ORDレコード
ord-cb613d474c1244ab84f3549f06c19176
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06939883B2

反応ノート

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