4-Aminopyridine → Methyl 2-(pyridin-4-ylamino)benzoxazole-4-carboxylate

HRID 249841ノート

反応式

HRID 249841 の反応式
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C([O-])([O-])=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(O)(C)C>[N:19]1[CH:20]=[CH:21][C:16]([NH:15][C:2]2[O:3][C:4]3[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=3)[N:6]=2)=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 17274-AminopyridineHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

生成物 1

HCID 66873583Methyl 2-(pyridin-4-ylamino)benzoxazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6386tert-Butanol溶媒

反応条件

温度
90 °C

実験手順

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (350 mg, 1.65 mmol), 4-aminopyridine (233 mg, 2.48 mmol), palladium(II) acetate (7.4 mg, 0.033 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (39 mg, 0.083 mmol), K2CO3 (570 mg, 4.13 mmol) and t-BuOH (4 mL) was heated to 90° C. for 40 min. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth and concentrated. The crude product was purified by column chromatography (silica gel, 9:1 CH2Cl2/CH3OH) to afford methyl 2-(pyridin-4-ylamino)benzoxazole-4-carboxylate. 1H NMR and MS consistent.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through diatomaceous earth
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, 9:1 CH2Cl2/CH3OH)

出典と根拠

ORDレコード
ord-64aad37a3af54c31889d64be9c5b2f5a
出典データセット
uspto-grants-2011_01
特許番号
US07863271B2

反応ノート

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