Tetrahydrofuran → HCID 11085875、化合物

HRID 402863ノート

反応式

HRID 402863 の反応式
Br[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C1COCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[O:4][CH:3]=2)=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 5212563-Bromochromone

生成物 1

HCID 11085875HCID 11085875、化合物収率 23%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

実験手順

Prepared according to general procedure using 3-bromochromone (338 mg, 1.5 mmol), 4-fluorophenylboronic acid (231 mg, 1.65 mmol), K2CO3 (622 mg, 4.5 mmol), PdCl2(PPh3)2 (45 mg, 0.045 mmol), THF (3 mL) and water (1.5 mL). Purified by flash column chromatography (SiO2, 10% EtOAc/Hex) to afford afford 37 (81 mg, 23%) as a white solid. Analytical data for isoflavone 37: 1H NMR (500 MHz, CDCl3) δ 8.34 (d, J=9 Hz, 1H), 8.04 (s, 1H), 7.72 (app t, J=9 Hz, 1H), 7.58-7.56 (m, 2H), 7.52 (d, J=8.5 Hz, 1H), 7.47 (app t, J=8 Hz, 1H), 7.16 (app t, J=9 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 176.5, 164.0, 162.0, 156.5, 153.2, 134.0, 131.0, 128.0, 126.7, 125.6, 124.8, 118.3, 115.8; LCMS: Mass calculated for C15H9FO2, [M+H]+, 241. Found 241.

後処理

  1. customPrepared
  2. customPurified by flash column chromatography (SiO2, 10% EtOAc/Hex)
  3. customto afford

出典と根拠

ORDレコード
ord-75277ca02b5542e6afaa7d2f9ac9042c
出典データセット
uspto-grants-2014_06
特許番号
US08742141B2

反応ノート

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