Potassium Carbonate → 4-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

HRID 530756노트

반응식

HRID 530756 반응식
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=1.[CH3:19][C:20]1[N:21]=[C:22]([Sn](CCCC)(CCCC)CCCC)[S:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=[C:2]([C:22]2[S:23][CH:24]=[C:20]([CH3:19])[N:21]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 164271304-Methyl-2-(tributylstannyl)-1,3-thiazoleHCID 866691142-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

생성물 1

HCID 681599974-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

To a solution of compound 21 (4.17 mmol) in DMF (15 mL) were added 4-methyl-2-(tributylstannyl)thiazole (5 mmol), dichlorobis(triphenylphosphine) palladium (II) chloride (0.417 mmol), and K2CO3 (5 mmol). The reaction mixture was stirred at 110° C. under microwave irradiations for 1 hr. 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: DCM) to give compound 22 in quantitative yield. MS (ESI, EI+): m/z=357.87 (MH+).

후처리

  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: DCM)

출처 및 근거

ORD 기록
ord-c1d5bf4eb9464ffeb9bf13fd7ee9b79f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353100B2

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