Pyridine → HCID 69687430, compound

HRID 1070397Notes

Reaction equation

HRID 1070397 reaction equation
[CH3:1][Si:2]([CH3:20])([CH3:19])[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[NH2:18])=[O:7].N1C=CC=CC=1.[C:27](Cl)(Cl)=[O:28].[C:31]1([C:37]2[CH:38]=[CH:39][C:40]3[O:44][C:43]([CH2:45][OH:46])=[CH:42][C:41]=3[CH:47]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:1][Si:2]([CH3:20])([CH3:19])[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[NH:18][C:27]([O:46][CH2:45][C:43]1[O:44][C:40]2[CH:39]=[CH:38][C:37]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:47][C:41]=2[CH:42]=1)=[O:28])=[O:7]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 113790942-Hydroxymethyl-5-phenyl-benzofuranHCID 69687024HCID 69687024, compound

Product 1

HCID 69687430HCID 69687430, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-amino-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (604 mg, 2.1 mmol) in toluene (12 mL) were added pyridine (0.34 mL, 4.21 mmol) and 20% phosgene in toluene (1.58 mL, 3.04 mmol) under a nitrogen atmosphere. The mixture was heated at 90° C. for 1.5 h, cooled to room temperature and filtered. The filtrate was concentrated to dryness. To the residue were added toluene (12 mL), (5-phenyl-benzofuran-2-yl)-methanol (471 mg, 2.10 mmol) and 4-dimethylaminopyridine (26 mg, 0.21 mmol) under a nitrogen atmosphere, and the mixture was heated at 90° C. for 16 h. Following dilution with EtOAc, the mixture was washed with 2N HCl, 10% NaHCO3, and brine, dried (Na2SO4) and concentrated to dryness. Purification by chromatography gave 582 mg of 2-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness
  4. temperaturethe mixture was heated at 90° C. for 16 h
  5. washthe mixture was washed with 2N HCl, 10% NaHCO3, and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness
  8. customPurification by chromatography

Sources & evidence

ORD record
ord-b90134133e434d7fa5e700a7bcc8d67e
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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