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

HRID 249841노트

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HRID 249841 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6386tert-Butanol용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-64aad37a3af54c31889d64be9c5b2f5a
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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