Triethylamine → tert-Butyl [[6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]carbamate

HRID 748845Notes

Reaction equation

HRID 748845 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])=[N:9][CH:10]=1)=[N+]=[N-].[H][H].C(N(CC)CC)C.[C:39](=O)([O:45]C(C)(C)C)[O:40][C:41]([CH3:44])([CH3:43])[CH3:42]>[Pd].ClCCl.CCCCCC.C(O)C.C(OCC)(=O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([CH:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[C:8]2[N:9]=[CH:10][C:5]([CH2:4][NH:1][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:6][CH:7]=2)(=[O:21])=[O:22])=[CH:24][CH:25]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 23114635HCID 23114635, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59750920tert-Butyl [[6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]carbamateYield 37%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 5-azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine (230 mg, 0.529 mmol) obtained in Example 350 and palladium on carbon (46 mg) were added to a mixture of ethyl acetate (15 ml) and ethanol (15 ml). The resulting mixture was stirred for 45 minutes under 1 atom hydrogen atmosphere. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane (5 ml). Triethylamine (70 μl, 0.499 mmol) and di-tert-butyl carbonate (174 mg, 0.996 mmol) were added to the resulting solution. The mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to flash chromatography on a silica gel column. A fraction obtained from the elution portion with hexane:ethyl acetate=4:1 was concentrated under reduced pressure, whereby title compound (78 mg, 0.153 mmol, 37%) was obtained as a colorless amorphous substance.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=4:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b823b12aaa541278eab3c9cf00f559a
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

Loading…