Triethylamine → HCID 68646448, compound

HRID 2237574Notes

Reaction equation

HRID 2237574 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][C:3]=1[F:15].C([N:18](CC)CC)C.[Br:23][CH2:24][C:25](Br)=[O:26]>C1COCC1>[Br:23][CH:24]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][C:3]=1[F:15])[C:25]([NH2:18])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromide2×HCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-one

Product 1

HCID 68646448HCID 68646448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

64.1 A solution of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (CAS 536747-52-1, prepared according to C. F. Bigge et al., patent application WO 2003045912) in 150 ml THF was treated with 5.8 ml triethylamine and 3.2 ml bromoacetyl bromide. The reaction mixture was stirred overnight at r.t., then again treated with 2.1 ml bromoacetyl bromide. After stirring overnight at r.t., the solid was filtered off and washed with THF. Then it was dissolved 11 EtOAc and washed 2× with 100 ml H2O. The organic layer was dried over MgSO4, filtered and concentrated to give 3.0 g 2-bromo-[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenyl]-acetamide as off-white solid. MS 325.1 ([M+H]+)

Workup

  1. stirringAfter stirring overnight at r.t.
  2. filtrationthe solid was filtered off
  3. washwashed with THF
  4. dissolutionThen it was dissolved 11 EtOAc
  5. washwashed 2× with 100 ml H2O
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3b5fec40ab914ce086cb17757ea95c56
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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