1,2-Dibromoethane → HCID 68712528, compound

HRID 1911501Notes

Reaction equation

HRID 1911501 reaction equation
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[CH:17]1[CH2:21][O:20][C:19]([NH2:22])=[N:18]1.[Br:23]CCBr>C1COCC1>[Br:23][C:15]1[C:10]([F:9])=[C:11]([CH:17]2[CH2:21][O:20][C:19]([NH2:22])=[N:18]2)[CH:12]=[CH:13][C:14]=1[F:16]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 2724682Lithium diisopropylamideHCID 59323878HCID 59323878, compound

Product 1

HCID 68712528HCID 68712528, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-55 °C

Procedure

A solution of lithium diisopropylamide in THF (2 M, 5.05 ml) was cooled to −55° C. and treated with (RS)-4-(2,4-difluoro-phenyl)-4,5-dihydro-oxazol-2-ylamine (667 mg, example 7) in THF (6 ml). The reaction mixture was stirred at −55° C. for 2 hrs, then treated dropwise with 1,2-dibromoethane (0.58 ml). The reaction mixture was warmed to r.t., then stirred overnight at r.t. It was quenched with H2O and extracted with EtOAc. The organic layer was dried over MgSO4, filtrated and concentrated. The crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 95:5) to give (RS)-4-(3-bromo-2,4-difluoro-phenyl)-4,5-dihydro-oxazol-2-ylamine (61 mg) as light yellow solid.

Workup

  1. temperatureThe reaction mixture was warmed to r.t.
  2. stirringstirred overnight at r.t
  3. customIt was quenched with H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-8308a1e5d9464f09b5bd6808417beed6
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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