Water → HCID 59200416, compound

HRID 1685296Notes

Reaction equation

HRID 1685296 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]C(C)(C)C.[NH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].Cl.O>C1COCC1>[NH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 178418306HCID 178418306, compound

Product 1

HCID 59200416HCID 59200416, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−78° C.), stirred solution of 2-bromopyridine (0.38 mL, 4.0 mmol) in THF (40 mL) under Ar was added dropwise t-BuLi (5.2 mL, 8.8 mmol). After 30 min, 2-aminoacetophenone•HCl (687 mg, 4.00 mmol) was added as a solid in one portion. The reaction was allowed to slowly warm to RT as the bath warmed. Water was added and the reaction mixture was extracted with EtOAc, dried (MgSO4), filtered and concentrated to afford a solid. Purification by flash chromatography afforded 68 mg as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 8.50 (d, J=4.80 Hz, 1H), 7.70-7.19 (m, 8H), 3.72 (d, J=13.14 Hz, 1H), 3.38 (d, J=13.14 Hz, 1H).

Workup

  1. temperaturewarmed
  2. extractionthe reaction mixture was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a solid
  7. customPurification by flash chromatography
  8. customafforded 68 mg as an oil

Sources & evidence

ORD record
ord-cd212933188b482a83fc297b808aff35
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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