HCID 10088037, compound → HCID 22277260, compound

HRID 1063869Notes

Reaction equation

HRID 1063869 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 22277260HCID 22277260, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c307f1065899499caba043568452bbb4
Source dataset
uspto-grants-2005_11
Patent number
US06967201B1

Reaction notes

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