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

HRID 2080402Notes

Reaction equation

HRID 2080402 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-].C(OCC)(=O)C.C(N(CC)CC)C.[C:43](=O)([O:49]C(C)(C)C)[O:44][C:45]([CH3:48])([CH3:47])[CH3:46]>ClCCl.[C].[Pd].CCCCCC.C(O)C>[C:45]([O:44][C:43](=[O:49])[NH:1][CH2:4][C:5]1[CH:10]=[N:9][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])=[CH:7][CH:6]=1)([CH3:48])([CH3:47])[CH3:46]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 23114635HCID 23114635, compound

Product 1

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

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

The 5-azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine (230 mg, 0.529 mmol) obtained in Example 62 and palladium 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 a hydrogen atmosphere of 1 atmospheric pressure. The reaction mixture was filtered. The filtrate was then concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane (5 ml). To the resulting solution were added triethylamine (70 μl, 0.499 mmol) and di-t-butyl carbonate (174 mg, 0.996 mmol). The resulting 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 silica gel column chromatography, and the fraction obtained from the hexane:ethyl acetate=4:1 eluate was concentrated under reduced pressure to give the title compound (78 mg, 0.153 mmol, 37%) as a colorless amorphous substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was then concentrated under reduced pressure
  3. customThe residue thus obtained
  4. stirringThe resulting mixture was stirred at room temperature for 3 days
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationethyl acetate=4:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d2e340a51a81491490659ff5aca9941b
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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