Bromine → HCID 91458778, compound

HRID 1171037Notes

Reaction equation

HRID 1171037 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:16][CH:15]=[N:14][C:13]=3[O:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:27]Br>CN(C=O)C>[Br:27][C:11]1[O:12][C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:18]=2[C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 91214691HCID 91214691, compound

Product 1

HCID 91458778HCID 91458778, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. solution of Example 27A (350 mg, 0.98 mmol) in DMF (10 mL) was treated with Br2 (0.102 mL, 1.98 mmol), warmed to room temperature, and stirred for 1 hour. The reaction was cooled to 0° C., quenched with 1:1 10% NaHSO3/saturated NaHCO3, and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated to provide 400 mg (93%) of the desired product. MS (ESI(−)) m/e 433, 435 (M−H)−.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 1:1 10% NaHSO3/saturated NaHCO3
  3. extractionextracted three times with ethyl acetate
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bbc3c91498d74d9cb9526adebcd3655e
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

Loading…