Sodium Carbonate → 6-(2-methoxyphenyl)-N-methyl-2-phenylpyrazolo[1,5-a]pyridine-3-carboxamide

HRID 219343노트

반응식

HRID 219343 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.I[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([N:19]=[C:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:21]=2[C:22]([NH:24][CH3:25])=[O:23])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([N:19]=[C:20]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:21]=2[C:22]([NH:24][CH3:25])=[O:23])[CH:18]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 592337926-iodo-N-methyl-2-phenylpyrazolo[1,5-a]pyridine-3-carboxamide

생성물 1

HCID 592337226-(2-methoxyphenyl)-N-methyl-2-phenylpyrazolo[1,5-a]pyridine-3-carboxamide수율 39.9%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

반응 조건

온도
150 °C

실험 절차

To a microwave vial equipped with a magnetic stir bar was charged 2-methoxyphenylboronic acid (12.09 mg, 0.080 mmol), 6-iodo-N-methyl-2-phenylpyrazolo[1,5-a]pyridine-3-carboxamide (15 mg, 0.040 mmol), sodium carbonate (7.38 mg, 0.070 mmol), palladium(II) acetate (0.893 mg, 3.98 μmol) and dimethylfomamide (1.0 mL). This mixture was placed under an argon atmosphere and heated at 150° C. for 10 minutes. The title compound (5.7 mg, 36%) was isolated by reverse phase HPLC: Start % B=30 to Final % B=80, Gradient time=10 minutes, Flow Rate=35 mL/minute, Wavelength=220 nm, Solvent A=10% methanol, 90% water with 0.1% TFA; Solvent B=90% methanol, 10% water with 0.1% TFA, Column=Phenomenex-Luna 30×50 mm S10, Product peak at 7.6 minutes. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 2.85 (d, J=4.88 Hz, 3H) 3.86 (s, 3H) 7.03 (d, J=7.93 Hz, 1H) 7.08 (t, J=7.02 Hz, 1H) 7.39 (m, 2H) 7.54 (m, 3H) 7.63 (dd, J=9.16, 1.53 Hz, 1H) 7.69 (m, 1H) 8.36 (dd, J=9.16, 0.61 Hz, 1H) 8.76 (m, 1H). LCMS: 2.0 minutes, M+1=358.

후처리

  1. customTo a microwave vial equipped with a magnetic stir bar

출처 및 근거

ORD 기록
ord-9659fcda0783417f9443234fe9432f7f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198449B2

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