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

HRID 1806090Notes

Reaction equation

HRID 1806090 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

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 mL, 267.0 mmol). The reaction was heated at 65° C. overnight and cooled to ambient temperature. LM 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).

Workup

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

Sources & evidence

ORD record
ord-bfec0a4a4a6b45c2af4f21b6cf4db37b
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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