Tetrahydrofuran → HCID 24720232, 화합물

HRID 402864노트

반응식

HRID 402864 반응식
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.[Cl:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=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>[Cl:13][C:14]1[CH:19]=[C:18]([CH:17]=[CH:16][CH:15]=1)[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

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 5212563-BromochromoneHCID 2734323(3-Chlorophenyl)boronic acid

생성물 1

HCID 24720232HCID 24720232, 화합물수율 50.1%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

실험 절차

Prepared according to general procedure using 3-bromochromone (338 mg, 1.5 mmol), 3-chlorophenylboronic acid (256 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 38 (193 mg, 50%) as a white solid. Analytical data for isoflavone 38: 1H NMR (500 MHz, CDCl3) δ 8.33 (d, J=9.5 Hz, 1H), 8.06 (s, 1H), 7.73 (app t, J=8.5 Hz, 1H), 7.60 (s, 1H), 7.59-7.45 (m, 3H), 7.39 (d, J=7 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 176.1, 156.4, 153.6, 134.6, 134.1, 133.9, 130.0, 129.2, 128.6, 127.4, 126.7, 125.7, 124.7, 124.5, 118.4; LCMS: Mass calculated for C15H9ClO2, [M+H]+, 257. Found 257.

후처리

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

출처 및 근거

ORD 기록
ord-b88fa85c2f964261b726818b4a0fc538
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742141B2

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