Sodium Carbonate → Ethyl 1-(2'-fluoro-2,3'-bipyridin-6-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255211

반응식

HRID 1255211 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Cl)[N:16]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].[F:22][C:23]1[C:28](B(O)O)=[CH:27][CH:26]=[CH:25][N:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[F:22][C:23]1[C:28]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([N:9]3[C:10]([C:11]([F:14])([F:13])[F:12])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]3)[N:16]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 73012968Ethyl 1-(6-chloropyridin-2-yl)-5-(trifluoromethyl)-1h-pyrazole-4-carboxylate

생성물 1

HCID 67158682Ethyl 1-(2'-fluoro-2,3'-bipyridin-6-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

A mixture of the title compound from Example 1 Step A (100 mg, 0.3 mmol), (2-fluoropyridin-3-yl)boronic acid (66 mg, 0.47 mmol), trans dichlorobis(triphenylphosphine) palladium (II) (31.0 mg, 0.05 mmol), Na2CO3 (0.47 mL, 2.0 M aqueous, 0.94 mmol) and acetonitrile (1 mL) in a nitrogen-filled capped vial was stirred at 100° C. After 50 min, the mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. Purification by flash chromatography on silica gel using hexane:EtOAc (6:1 to 4:1 v/v) as mobile phase provided the title compound: LCMS m/z 381.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 8.63 (m, 1H), 8.27 (m, 1H), 8.13 (s, 1H), 8.10 (d, J=7.9 Hz, 1H), 8.03 (t, J=7.9 Hz, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.35 (m, 1H), 4.39 (q, J=7.1 Hz, 2H), 1.39 (t, J=7.1 Hz, 3H).

후처리

  1. additionfilled
  2. customcapped vial
  3. temperatureto cool to ambient temperature
  4. concentrationwas concentrated in vacuo
  5. customPurification by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-ed68d44c48914655a645010660c3baa1
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455638B2

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