Pyridine → Benzyl (4-chloropyridin-3-yl)carbamate

HRID 69950

Reaction equation

HRID 69950 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[Cl:19].N1C=CC=CC=1>C1COCC1>[Cl:19][C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 5819323-Amino-4-chloropyridine

Product 1

HCID 69042933Benzyl (4-chloropyridin-3-yl)carbamateYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzyl chloroformate (1.1 equiv.) in THF (1.85 M) was slowly added to a solution of 3-amino-4-chloropyridine (1.0 equiv.) and pyridine (1.5 equiv.) in THF (1.0 M) and stirred at rt for 3.5 hours (formation of a precipitate over time). The reaction was quenched with H2O (100 mL), extracted with EtOAc (200 mL), washed with NaCl(sat.) (75 mL), dried over MgSO4, filtered and the volatiles were removed in vacuo. The product precipitated from a mixture of hexane/EtOAc yielding benzyl 4-chloropyridin-3-ylcarbamate (34%). LCMS (m/z): 263.1 (MH+); LC Rt=2.33 min.

Workup

  1. customThe reaction was quenched with H2O (100 mL)
  2. extractionextracted with EtOAc (200 mL)
  3. washwashed with NaCl(sat.) (75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe volatiles were removed in vacuo
  7. customThe product precipitated from a mixture of hexane/EtOAc

Sources & evidence

ORD record
ord-fe4cb553cd4346b4a655937987b025fe
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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