Ethylene glycol diethyl ether → Prinaberel

HRID 858239

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HRID 858239 반응식
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([OH:19])[CH:3]=1.[CH2:20]([Sn](CCCC)(CCCC)C=C)[CH2:21]CC.C(OCCOCC)C>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[F:18][C:13]1[CH:12]=[C:11]([C:8]2[O:9][C:10]3[C:2]([CH:20]=[CH2:21])=[CH:3][C:4]([OH:19])=[CH:5][C:6]=3[N:7]=2)[CH:16]=[CH:15][C:14]=1[OH:17]

참가 물질

5

반응물 3

HCID 12375Ethylene glycol diethyl etherHCID 81998TributylvinyltinHCID 1354573257-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

생성물 1

HCID 656954Prinaberel수율 72.6%

시약·촉매·용매 1

HCID 178424406HCID 178424406, 화합물촉매

반응 조건

온도
115 °C

실험 절차

Dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 1.1 mmol) was added into a mixture of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (7.16 g, 22.1 mmol), tributyl(vinyl)tin (10.5 g, 33.25 mmol) and ethylene glycol diethyl ether (65 mL). The reaction mixture was stirred at 115° C. for 48 h, cooled to room temperature and treated with activated carbon. The mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography, on acidic silica gel (hexanes/EtOAc/CH2Cl2 1/1/1), gave a white solid (4.35 g, 72% yield, m.p. 250–252° C.); MS m/e 272 (M+H)+.

후처리

  1. temperaturecooled to room temperature
  2. additiontreated with activated carbon
  3. filtrationThe mixture was filtered through MgSO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-1019434c6a5e4d468528111ddbb17ee5
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148247B2

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