Pyridine → Phenyl carbamate

HRID 1168730Notes

Reaction equation

HRID 1168730 reaction equation
[NH2:1]N1C2C=NC=CC=2C2C1=CC(Cl)=CC=2.N1C=CC=CC=1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>C1COCC1>[C:23](=[O:24])([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH2:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 221852799-Amino-7-chloro-beta-carboline

Product 1

HCID 69322Phenyl carbamateYield 224%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cold (3° C. to 5° C.) solution of the product of example 15 (30 mg, 0.14 mmol) and pyridine (0.014 ml, 0.17 mmol) in THF (0.7 ml) was treated with phenyl chloroformate (0.018 ml, 0.145 mmol). After stirring at RT for 2 h, the reaction was partitioned in ethyl acetate and buffer (pH 7.2). The organic layer was dried (brine, Na2SO4) and concentrated to give 43 mg of phenyl carbamate.

Workup

  1. customthe reaction was partitioned in ethyl acetate
  2. dry with materialThe organic layer was dried (brine, Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5fb0ea01cfea4463b1d57332335fae26
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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