Water → HCID 69687024, compound

HRID 1070396Notes

Reaction equation

HRID 1070396 reaction equation
[CH3:1][Si:2]([CH3:27])([CH3:26])[CH2:3][CH2:4][O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1OS(C(F)(F)F)(=O)=O)=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].C(=[NH:47])(C1C=CC=CC=1)C1C=CC=CC=1.O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][Si:2]([CH3:27])([CH3:26])[CH2:3][CH2:4][O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[NH2:47])=[O:7]

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 86586341HCID 86586341, compound

Product 1

HCID 69687024HCID 69687024, compoundYield 62.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (4.22 g, 10.0 mmol) in THF (40 mL) were added cesium carbonate (4.58 g, 14.05 mmol), palladium acetate (0.067 g, 0.3 mmol), BINAP (0.28 g, 0.45 mmol) and benzophenone imine (2.0 mL, 12.04 mmol) under an argon atmosphere. The mixture was heated at 65° C. for 16 h. After addition of water the mixture was extracted with EtOAc, washed with brine, dried (Na2SO4) and concentrated to dryness. To the residue were added THF (40 mL), methyl alcohol (10 mL) and 2N HCl (6.6 mL), and the mixture was stirred for 2 h at room temperature. After addition of 10% NaHCO3 the mixture was extracted, dried (Na2SO4) and concentrated to dryness. Purification by chromatography gave 1.8 g of 2-amino-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester.

Workup

  1. extractionwas extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to dryness
  5. additionTo the residue were added THF (40 mL), methyl alcohol (10 mL) and 2N HCl (6.6 mL)
  6. additionAfter addition of 10% NaHCO3 the mixture
  7. extractionwas extracted
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to dryness
  10. customPurification by chromatography

Sources & evidence

ORD record
ord-bc411496fc0a405896c4e6213e936372
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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