Potassium Carbonate → HCID 67975593, 화합물

HRID 2046236노트

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HRID 2046236 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:15](I)=[C:9]2[C:10](=[O:14])[NH:11][CH2:12][CH2:13][N:8]2[N:7]=1)=[O:5])[CH3:2].[CH3:17]B(O)O.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+]>C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15]([CH3:17])=[C:9]2[C:10](=[O:14])[NH:11][CH2:12][CH2:13][N:8]2[N:7]=1)=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 679916203-Iodo-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine-2-carboxylic acid ethyl ester

생성물 1

HCID 67975593HCID 67975593, 화합물수율 58.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 10340Sodium Carbonate용매

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온도
90 °C

실험 절차

Palladium (II) acetate (38 mg, 0.17 mmol) was added to a solution of 3-iodo-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine-2-carboxylic acid ethyl ester (0.56 g 1.68 mmol), methylboronic acid (0.75 g, 12.6 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triiso-propyl-1,1′-biphenyl (0.16 mg, 0.34 mmol) and potassium carbonate (0.69 g, 5.0 mmol) in toluene (15 mL) under nitrogen and the mixture was heated at 90° C. for 16 hours. Then the mixture was heated at 120° C. for 4 hours more. The mixture was diluted with a saturated Na2CO3 solution and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 3-methyl-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine-2-carboxylic acid ethyl ester (0.22 g, 58% yield).

후처리

  1. temperatureThen the mixture was heated at 120° C. for 4 hours more
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica; MeOH in DCM 0/100 to 10/90)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

출처 및 근거

ORD 기록
ord-beb72d1493d945f8a007fe14f4cab420
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592422B2

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