Potassium Carbonate → 2',6'-Dimethyl-biphenyl-3-carboxylic acid amide

HRID 227901

反応式

HRID 227901 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].O>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[CH:3]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 692543-ChlorobenzamideHCID 5833222,6-Dimethylphenylboronic acid

生成物 1

HCID 116371732',6'-Dimethyl-biphenyl-3-carboxylic acid amide収率 92%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate触媒HCID 962Water溶媒

実験手順

Using microwave irradiation. The general procedure described in Example 3 was used with 3-chlorobenzamide (156 mg, 1.00 mmol), 2,6-dimethylphenylboronic acid (180 mg, 1.20 mmol), Pd(OAc)2 (4.5 mg, 0.020 mmol, 2 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (20.0 mg, 0.0391 mmol, 4 mol %), K2CO3 (345 mg, 2.50 mmol), water (3.0 mL), 10 min, 150° C. (microwave irradiation with cooling). The product was isolated as a white solid (207 mg, 92%). Mp=123-125° C. 1H NMR (400 MHz, CDCl3) δ: 7.85 (d, 1H, J=7.6 Hz), 7.67 (s, 1H), 7.50 (t, 1H, J=7.6 Hz), 7.33 (d, 1H, J=7.6 Hz), 7.20 (t, 1H, J=7.4 Hz), 7.13 (d, 2H, J=7.2 Hz), 6.87 (br-s, 1H), 6.69 (br-s, 1H), 2.03 (s, 6H). 13C NMR (125 MHz, CDCl3) δ: 170.1, 141.6, 140.8, 135.9, 133.8, 132.8, 128.9, 128.1, 127.5, 126.0, 20.96. IR (neat, cm−1): 3347 (br), 3197 (br), 1657, 1602, 1578, 1379, 1102, 770, 737, 703. Anal. Calcd for C15H15NO: C, 79.97; H, 6.71. Found: C, 79.98; H, 6.48.

後処理

  1. custommicrowave irradiation

出典と根拠

ORDレコード
ord-9895f6602c0245fd82316921168589ff
出典データセット
uspto-grants-2009_07
特許番号
US07560596B2

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