Acetic Acid Mixture with Hydrobromic Acid → HCID 59375658, compound

HRID 2193035Notes

Reaction equation

HRID 2193035 reaction equation
C([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16]([CH3:18])=[CH2:17])=[N:11]2)CCC.[BrH:24].C(O)(=O)C>>[Br:24][CH2:17][CH:16]([C:10]1[C:9]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:8]=2[C:7]2[C:6](=[O:5])[NH:15][CH:14]=[CH:13][C:12]=2[N:11]=1)[CH3:18]

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 59375395HCID 59375395, compound

Product 1

HCID 59375658HCID 59375658, compound

Procedure

A solution of 1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine (26 mg, 0.063 mmol) in HBr/acetic acid (33% wt) (1.0 ml) was stirred for 18 hr at room temperature. The reaction mixture was concentrated to a crude solid that was taken up into acetonitrile (5 mL) and concentrated again in an attempt to drive off more acetic acid. The resulting solid was triturated with EtOAc (1 mL), then collected by vacuum filtration to afford 6-(2-bromo-1-methylethyl)-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one (HBr salt). LRMS (ESI) calc'd for (C15H12BrFN2O) [M+H]+, 335.0; found 335.0.

Workup

  1. concentrationThe reaction mixture was concentrated to a crude solid that
  2. concentrationconcentrated again in an attempt
  3. customThe resulting solid was triturated with EtOAc (1 mL)
  4. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-938ff91af3264193a5def299af1a378c
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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