Hydrochloric Acid → 5-Benzyloxy-pyridin-2-ylamine hydrochloride

HRID 335163

反応式

HRID 335163 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-:18][Si](C)(C)C.[Li+].Cl.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].C1COCC1>[ClH:15].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 100137175-(Benzyloxy)-2-chloropyridine

生成物 1

HCID 669951705-Benzyloxy-pyridin-2-ylamine hydrochloride収率 98.94%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To a nitrogen purged solution of mL Pd2 (dba)3 (10.19 g, 11.12 mmol), 5-(benzyloxy)-2-chloropyridine (48.87 g, 222.5 mmol), (2-diphenyl)dicyclohexyl-phosphine (7.797 g, 22.25 mmol) and THF (700 mL) was added lithium hexamethyl disilazide (267.0 mL, 267.0 mmol). The reaction was heated at 65° C. overnight and cooled to ambient temperature. 1M HCl (250 mL) was added and stirred for minutes. Saturated sodium bicarbonate was added slowly. The mixture was extracted several times with CH2Cl2, dried, filtered, and concentrated to give the title compound (52.1 g, 98.94% yield).

後処理

  1. temperaturecooled to ambient temperature
  2. extractionThe mixture was extracted several times with CH2Cl2
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-df42bb9ffab44f3180050693d20fa6f0
出典データセット
uspto-grants-2014_11
特許番号
US08883828B2

関連ノート

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