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

HRID 1247229ノート

反応式

HRID 1247229 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178424406HCID 178424406、化合物触媒HCID 7809P-Xylene溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-a7060fac4add49a09db196d41ff765cb
出典データセット
uspto-grants-2006_10
特許番号
US07129258B2

反応ノート

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