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

HRID 710565ノート

反応式

HRID 710565 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-80acb594515e4a3e8b8041eb50c67780
出典データセット
uspto-grants-2015_11
特許番号
US09181238B2

反応ノート

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