HCID 10088037, 화합물 → HCID 22277260, 화합물

HRID 1063869노트

반응식

HRID 1063869 반응식
[F:1][C:2]1[CH:3]=[C:4](Br)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[C:12]1([C:18]([NH:31][CH2:32][C:33]([NH2:36])([CH3:35])[CH3:34])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:12]1([C:18]([NH:31][CH2:32][C:33]([NH:36][C:4]2[C:5]3[O:9][CH:8]=[CH:7][C:6]=3[CH:10]=[C:2]([F:1])[CH:3]=2)([CH3:34])[CH3:35])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 3

HCID 10088037HCID 10088037, 화합물HCID 221448167-Bromo-5-fluoro-1-benzofuranHCID 23676156Sodium t-butoxide

생성물 1

HCID 22277260HCID 22277260, 화합물수율 70.2%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

A mixture of 5.0 gm (23.3 mmol) 5-fluoro-7-bromobenzofuran, 10.3 gm (32.6 mmol) 1-(triphenylmethyl)amino-2-amino-2-methylpropane, 0.87 gm (1.4 mMol) racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 0.64 gm (0.7 mMol) tris(dibenzylideneacetone)dipalladium, and 3.13 gm (32.5 mMol) sodium tert-butoxide in 60 ml anhydrous toluene was degassed and purged with nitrogen. The reaction mixture was heated at reflux for 2 hours and was then allowed to cool to room temperature. The reaction mixture was diluted with 50 mL diethyl ether, filtered through celite, and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 15:1 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 7.6 gm (70%) of the desired product.

후처리

  1. customwas degassed
  2. custompurged with nitrogen
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 2 hours
  5. additionThe reaction mixture was diluted with 50 mL diethyl ether
  6. filtrationfiltered through celite
  7. concentrationthe filtrate concentrated under reduced pressure
  8. washeluting with 15:1 hexane
  9. additionFractions containing product
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c307f1065899499caba043568452bbb4
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967201B1

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