Potassium Carbonate → tert-Butyl 2-(3-chloro-6-oxopyridazin-1(6H)-yl)ethylcarbamate

HRID 1878747Notes

Reaction equation

HRID 1878747 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][N:7]=1.Br[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2528286-Chloropyridazin-3-olHCID 516892Sodium BicarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 59843113tert-Butyl 2-(3-chloro-6-oxopyridazin-1(6H)-yl)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 6-chloropyridazin-3(2H)-one (2912 mg, 22.3 mmol), tert-butyl 2-bromoethylcarbamate (5000 mg, 22.3 μmol), and K2CO3 (9251 mg, 66.9 mmol) was stirred in DMF (40 mL) overnight at 23° C. The mixture was partioned between CH2Cl2 (200 mL) and 5% NaHCO3 (50 mL). The organic layer was dried with brine and MgSO4, concentrated to a solid from toluene under reduced pressure. MS (ESI pos. ion) m/z (MH+): 274 Calc'd exact mass for C11H16ClN3O3: 273.

Workup

  1. dry with materialThe organic layer was dried with brine and MgSO4
  2. concentrationconcentrated to a solid from toluene under reduced pressure

Sources & evidence

ORD record
ord-16c096172e454721815ee0f329cb584b
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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