N-methyl-2-pyrrolidone → HCID 67452526, compound

HRID 2276751Notes

Reaction equation

HRID 2276751 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=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>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([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)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 1522141-PhenylcyclobutylamineHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 67452526HCID 67452526, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a 20 dram vial was added 5-bromo-2-fluoropyridine (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 extracted with ethyl acetate (50 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography to give 102 mg (26%) of 5-bromo-N-(1-phenylcyclobutyl)pyridin-2-amine as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid that
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-be42712e827544a59cd73a60acad6f04
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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