N-methyl-2-pyrrolidone → HCID 67454264, compound

HRID 2276749Notes

Reaction equation

HRID 2276749 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.[C:9]1([C:15]2([NH2:19])[CH2:18][CH2:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN1C(=O)CCC1>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:19][C:15]2([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:16][CH2:17][CH2:18]2)[CH:3]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 1522141-PhenylcyclobutylamineHCID 38477704-Bromo-2-chloropyridine

Product 1

HCID 67454264HCID 67454264, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a 20 dram vial was added 4-bromo-2-chloropyridine (250 mg, 5.0 mmol, 1.0 equiv), 1-phenylcyclobutanamine (1.0 g, 7 mmol, 1.4 equiv), and NMP (1 mL). The reaction was heated to 120° C., stirred for 72 h, and then diluted with water (20 mL) and ethyl acetate (50 mL). After transferring to a separatory funnel and shaking, the organic layer was separated from the aqueous layer. The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography, affording 139 mg (9%) of 4-bromo-N-(1-phenylcyclobutyl)pyridin-2-amine as an orange solid.

Workup

  1. customAfter transferring to a separatory funnel
  2. stirringshaking
  3. customthe organic layer was separated from the aqueous layer
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude solid that
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-149d0b0e690c43419d05d17a83817bb0
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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