Pyridine → Phenyl carbamate

HRID 1795092Notes

Reaction equation

HRID 1795092 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-ba3a98bdff964aee987ff1e8d456f842
Source dataset
uspto-grants-2006_04
Patent number
US07026331B2

Reaction notes

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