Methyl N-(triethylammoniosulfonyl)carbamate → 2-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

HRID 530755Notes

Reaction equation

HRID 530755 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:9][CH2:10][C:11]([C:14]([F:17])([F:16])[F:15])(O)[N:12]=2)[CH:5]=[C:4]([O:18][CH3:19])[CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[CH:5]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:14]([F:17])([F:15])[F:16])[N:12]=2)[N:7]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 866691152-(6-Chloro-4-methoxy-pyridin-2-yl)-4-trifluoromethyl-4,5-dihydro-thiazol-4-ol

Product 1

HCID 866691142-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridineYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 20 (8.67 mmol) in THF (30 mL) was added Burgess Reagent (9.5 mmol). The reaction mixture was stirred at 60° C. for 30 min. The solution was concentrated in vacuo and H2O and DCM were added. The layers were separated and the organic layer was concentrated. The crude was purified by silica gel chromatography (eluent: petroleum ether/DCM 50 to 100%) to give compound 21 as a beige solid in 48% yield. MS (ESI, EI+): m/z=294.87 (MH+).

Workup

  1. concentrationThe solution was concentrated in vacuo and H2O and DCM
  2. additionwere added
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated
  5. customThe crude was purified by silica gel chromatography (eluent: petroleum ether/DCM 50 to 100%)

Sources & evidence

ORD record
ord-035de6ad101646ddb373b359051a1b1a
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

Loading…