4-Methoxybenzylamine → 3,5-Difluoro-N4-(4-methoxybenzyl)pyridine-2,4-diamine

HRID 710565노트

반응식

HRID 710565 반응식
[F:1][C:2]1[C:3]([NH2:10])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1I.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].C(=O)(O)[O-].[Na+]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([NH2:10])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[NH:18][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1

참가 물질

8

반응물 5

HCID 754524-MethoxybenzylamineHCID 516892Sodium BicarbonateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 673650093,5-Difluoro-4-iodopyridin-2-amine

생성물 1

HCID 673672603,5-Difluoro-N4-(4-methoxybenzyl)pyridine-2,4-diamine

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
130 °C

실험 절차

A stirred mixture of 3,5-Difluoro-4-iodopyridin-2-amine (3.0 g, 11.7 mmol), 4-methoxybenzylamine (1.92 g, 14 mmol), Pd2dba3 (1.07 g, 1.2 mmol), BINAP (1.46 g, 2.3 mmol), sodium t-butoxide (1.46 g, 2.3 mmol), and toluene (600 ml) was heated in a sealed vessel with stirring at 130° C. for 16 h. Aqueous sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel (30% ethyl acetate in hexanes eluant) to provide the title compound.

후처리

  1. temperaturewas heated in a sealed vessel
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (30% ethyl acetate in hexanes eluant)

출처 및 근거

ORD 기록
ord-80acb594515e4a3e8b8041eb50c67780
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181238B2

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