4-Formylphenylboronic Acid → 7-[(2,4-Dichloro-5-methoxyphenyl)amino]-3-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile

HRID 1178683ノート

反応式

HRID 1178683 の反応式
Br[C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:22]#[N:23])[C:10]([NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([Cl:20])=[CH:14][C:13]=3[Cl:21])=[C:5]2[S:4][CH:3]=1.[CH:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25]>COCCOC.C(=O)(O)[O-].[Na+]>[Cl:21][C:13]1[CH:14]=[C:15]([Cl:20])[C:16]([O:18][CH3:19])=[CH:17][C:12]=1[NH:11][C:10]1[C:9]([C:22]#[N:23])=[CH:8][N:7]=[C:6]2[C:2]([C:29]3[CH:30]=[CH:31][C:26]([CH:24]=[O:25])=[CH:27][CH:28]=3)=[CH:3][S:4][C:5]=12

参加物

5

反応物 2

HCID 5910734-Formylphenylboronic AcidHCID 113962683-Bromo-7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile

生成物 1

HCID 117513977-[(2,4-Dichloro-5-methoxyphenyl)amino]-3-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile収率 61.7%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of 3-bromo-7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile (1.67 g, 3.89 mmol), 4-formylphenyl boronic acid (1.17 g, 7.78 mmol), and tetrakis(triphenylphosphine)pallidium (225 mg, 0.20 mmol) in 50 mL of ethylene glycol dimethyl ether and 42 mL of saturated aqueous sodium bicarbonate is heated at reflux for 2 hours and then cooled to room temperature. The precipitate is collected by filtration washing with ethyl acetate and diethyl ether to provide 1.09 g of 7-[(2,4-dichloro-5-methoxyphenyl)amino]-3-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile as a tan solid, mp 268° C. dec; 1H NMR (DMSO-d6) δ 3.87 (s, 3H), 7.44 (s, 1H), 7.79 (s, 1H), 8.01 (d, J=8 Hz, 2H), 8.23 (d, J=8 Hz, 2H), 8.55 (s, 1H), 8.73 (s, 1H), 9.86 (s, 1H), 10.05 (s, 1H); MS 454.0, 456.0 (M+H)+; HRMS found: 454.01716 (M+H)+.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe precipitate is collected by filtration
  4. washwashing with ethyl acetate and diethyl ether

出典と根拠

ORDレコード
ord-159712cdce714ebca497416ad1ce0474
出典データセット
uspto-grants-2007_10
特許番号
US07276519B2

反応ノート

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