HCID 10088037、化合物 → HCID 22277260、化合物

HRID 1063869ノート

反応式

HRID 1063869 の反応式
[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

参加物

7

反応物 3

HCID 10088037HCID 10088037、化合物HCID 221448167-Bromo-5-fluoro-1-benzofuranHCID 23676156Sodium t-butoxide

生成物 1

HCID 22277260HCID 22277260、化合物収率 70.2%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c307f1065899499caba043568452bbb4
出典データセット
uspto-grants-2005_11
特許番号
US06967201B1

反応ノート

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