2-(Tributylstannyl)furan → 7-(2-Furyl)-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole

HRID 1247229노트

반응식

HRID 1247229 반응식
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:26]1[O:27][CH:28]=[CH:29][CH:30]=1)CCC>CC1C=CC(C)=CC=1.[Cl-].[NH4+].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>[O:27]1[CH:28]=[CH:29][CH:30]=[C:26]1[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1

참가 물질

6

반응물 2

HCID 43936882-(Tributylstannyl)furanHCID 121489697-Bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole

생성물 1

HCID 219073927-(2-Furyl)-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole수율 99%

시약·촉매·용매 3

HCID 178424406HCID 178424406, 화합물촉매HCID 7809P-Xylene용매HCID 25517Ammonium Chloride용매

실험 절차

7-Bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole (300 mg, 0.90 mmol) and dichlorobis(tri-o-tolylphosphine)palladium(II) (71 mg, 0.09 mmol) were dissolved in p-xylene (3 mL) and stirred for 10 min at room temperature under a nitrogen atmosphere. 2-(Tributylstannyl)furan (449 mg, 1.26 mmol) was added and the mixture was refluxed for 4 hours. The mixture was cooled to room temperature, diluted with a saturated solution of ammonium chloride and extracted with EtOAc. The organic extracts were washed with water, then brine and dried over MgSO4 and concentrated. Purification by flash chromatography (20%–30% EtOAc/petroleum ether) gave the title compound as a white solid (99% yield, m.p. 120–121° C.); MS m/e 322 (M+H)+.

후처리

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with water
  5. dry with materialbrine and dried over MgSO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20%–30% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-a7060fac4add49a09db196d41ff765cb
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129258B2

반응 노트

불러오는 중…