Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate → 10-Bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylic acid

HRID 575044Notes

Reaction equation

HRID 575044 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[F:16])[CH:12]1[CH2:17][CH:10]([CH2:11]1)[N:9]1[C:5]2=[N:6][C:7]([C:18]([O:20]C)=[O:19])=[CH:8]1>CO.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[F:16])[CH:12]1[CH2:11][CH:10]([CH2:17]1)[N:9]1[C:5]2=[N:6][C:7]([C:18]([OH:20])=[O:19])=[CH:8]1

Participants

3

Reactant 1

HCID 86693079Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Product 1

HCID 8669307810-Bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylic acidYield 86.2%

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

Into a 5000-mL 4-necked round-bottom flask was placed a solution of methyl 9-bromo-10-fluoro-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxylate (110 g, 313.24 mmol, 1.00 equiv) in methanol/NaOH (40%) (1000 mL). The resulting solution was heated to reflux for 1.5 hours and concentrated under vacuum. Hydrogen chloride (2 mol/L) was used to adjust the pH to 4. The precipitates were collected by filtration, washed with 1×1000 mL of water and dried to afford 91 g (86%) of 9-bromo-10-fluoro-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxylic acid as a white solid.

Workup

  1. customInto a 5000-mL 4-necked round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 1.5 hours
  4. concentrationconcentrated under vacuum
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with 1×1000 mL of water
  7. customdried

Sources & evidence

ORD record
ord-64836001e655436f8ca762236a91e45f
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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