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

HRID 335163

반응식

HRID 335163 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 669951705-Benzyloxy-pyridin-2-ylamine hydrochloride수율 98.94%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-df42bb9ffab44f3180050693d20fa6f0
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883828B2

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