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

HRID 1178683노트

반응식

HRID 1178683 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-159712cdce714ebca497416ad1ce0474
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276519B2

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