Triethylamine → 5-(4-bromo-2-chlorophenyl)-4-fluoro-5H-imidazo[4',5':4,5]benzo[1,2-d]oxazol-6(7H)-one

HRID 928982Notes

Reaction equation

HRID 928982 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10](C(O)=O)=[CH:11][C:12]3[O:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([Cl:22])[CH:3]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])=CC=1.C([N:42]([CH2:45]C)CC)C>CC(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3[C:10](=[CH:11][C:12]4[O:16][CH:15]=[N:14][C:13]=4[C:17]=3[F:18])[NH:42][C:45]2=[O:30])=[C:4]([Cl:22])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 897048215-((4-Bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid

Product 1

HCID 897053695-(4-bromo-2-chlorophenyl)-4-fluoro-5H-imidazo[4',5':4,5]benzo[1,2-d]oxazol-6(7H)-oneYield 96.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 5-((4-bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid (110 mg, 0.28 mmol) in t-BuOH (3 mL) was added DPPA (94 mg, 0.34 mmol) followed by triethylamine (58 mg, 0.57 mmol). The mixture was heated under reflux for 3 h and allowed to slowly warm to room temperature. The solvent was removed in vacuo and the resultant crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 2:1, v/v). The corresponding product was obtained (white solid, 105 mg, 96.2% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.78 (s, 1H), 8.69 (s, 1H), 7.99 (d, 1H), 7.77 (d, 1H), 7.51 (m, 1H), 7.41 (s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was removed in vacuo
  4. customthe resultant crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 2:1
  5. customThe corresponding product was obtained (white solid, 105 mg, 96.2% yield)

Sources & evidence

ORD record
ord-cb4dfbc4ca6b43d4b3e1c086de1df629
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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