Potassium Phosphate, Tribasic → 6-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)pyridazin-3-amine

HRID 449647

반응식

HRID 449647 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[N:15]=[N:14][C:13]([NH2:16])=[CH:12][CH:11]=1.[Cl-].[CH3:18][NH+:19]1[CH2:24][CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH2:21][CH2:20]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C(O)CCC.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:18][N:19]1[CH2:20][CH:21]=[C:22]([C:10]2[N:15]=[N:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:23][CH2:24]1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27947796-Bromopyridazin-3-amineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 667428051-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridinium chloride

생성물 1

HCID 667428086-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)pyridazin-3-amine수율 82%

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 2631-Butanol용매HCID 962Water용매

반응 조건

온도
115 °C

실험 절차

In a 15 mL microwave reaction vial was added potassium phosphate tribasic (1.43 g, 6.74 mmol), 6-bromopyridazin-3-amine (335 mg, 1.93 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridinium chloride (500 mg, 1.93 mmol), X-PHOS (138 mg, 289 μmol) and bis(dibenzylideneacetone)palladium (83 mg, 144 μmol) in 7 mL n-butanol and 1.4 mL H2O. The tube was sealed under argon and heated at 115° C. in oil bath for 3 hrs then stirred at room temperature overnight. The phases were separated and the aqueous was extracted with EtOAc. (10 ml). Water (20 mL) was added to the residual aqueous phase and was extracted with DCM (3×10 mL). The extracts were combined with the EtOAc organic phase. The resultant solution was absorbed onto silica gel and purified by LC chromatography eluting with 0-10% (10% NH4OH in MeOH) in 1/1 EtOAc/hexane to afford 300 mg (82%) of the title compound.

후처리

  1. customIn a 15 mL microwave reaction
  2. customThe tube was sealed under argon
  3. customThe phases were separated
  4. extractionthe aqueous was extracted with EtOAc
  5. additionWater (20 mL) was added to the residual aqueous phase
  6. extractionwas extracted with DCM (3×10 mL)
  7. customThe resultant solution was absorbed onto silica gel
  8. custompurified by LC chromatography
  9. washeluting with 0-10% (10% NH4OH in MeOH) in 1/1 EtOAc/hexane

출처 및 근거

ORD 기록
ord-cafd7974e6f74ac290c8eed5ebf44287
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481540B2

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