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

HRID 44023ノート

反応式

HRID 44023 の反応式
[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.CN(C)C=O>[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

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 mmol) and dimethylforamide (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, 1 H). LCMS: 2.0 minutes, M+1=358.

後処理

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

出典と根拠

ORDレコード
ord-18c4d111fd634c16a18990f910a54d0d
出典データセット
uspto-grants-2013_09
特許番号
US08536338B2

反応ノート

読み込み中…