Dimethylformamide → HCID 58204448, compound

HRID 1498154Notes

Reaction equation

HRID 1498154 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)=[C:6]([OH:8])[CH:7]=1.CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27]Br>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[N:13]([CH:12]=[CH:11][N:10]=3)[CH2:26][CH2:27][O:8][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 135742037HCID 135742037, compound

Product 1

HCID 58204448HCID 58204448, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

5-fluoro-2-(1H-imidazole-2-yl)phenol (0.90 g, 5.0 mmol) was dissolved in N,N-Dimethylformamide (40 mL, 500 mmol). Cesium carbonate (6.6 g, 20 mmol) was added, followed by 1,2-Dibromoethane (1.7 mL, 20 mmol) and heated at 90° C. with a vigreux condensation column attached for 3 hours. Complete by LCMS. Diluted with water and extracted with ethyl acetate. Acidified the aqueous layer to pH ˜5 with HCl and extracted with ethyl acetate. The combined organics were concentrated in vacuo and purified by flash chromatography on the ISCO 0-50% ethyl acetate in hexanes and concentrated in vacuo to give 9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (0.69 g, 67% yield)

Workup

  1. extractionextracted with ethyl acetate
  2. extractionAcidified the aqueous layer to pH ˜5 with HCl and extracted with ethyl acetate
  3. concentrationThe combined organics were concentrated in vacuo
  4. custompurified by flash chromatography on the ISCO 0-50% ethyl acetate in hexanes
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca47243793ed47ac882eb87b7286d5c9
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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