Bromoacetyl bromide → HCID 10272492, compound

HRID 1582456Notes

Reaction equation

HRID 1582456 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][CH2:6][C:7](Br)=[O:8].[F:10][C:11]([F:29])([F:28])[C:12]([N:14]1[CH2:27][CH2:26][C:18]2=[CH:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[N:17]2[CH2:16][CH2:15]1)=[O:13].C([O-])(O)=O.[Na+]>ClCCl>[Br:5][CH2:6][C:7]([C:19]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[N:17]2[CH2:16][CH2:15][N:14]([C:12](=[O:13])[C:11]([F:29])([F:28])[F:10])[CH2:27][CH2:26][C:18]=12)=[O:8]

Participants

6

Reactant 4

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 9921822HCID 9921822, compound

Product 1

HCID 10272492HCID 10272492, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(Chart E, Step 1): A dry round bottom flask is charged with AlCl3 (66.7 mg, 0.5 mmol) and dichloromethane (4 mL) to make a heterogeneous solution. Dropwise addition of bromo-acetylbromide (0.044 mL, 0.5 mmol) turns the reaction into a homogeneous orange solution. After 30 minutes of stirring at ambient temperature, a solution of 2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl)-1-ethanone (141.1 mg, 0.5 mmol) in dichloromethane (2 mL) is added dropwise and stirred for three days. The reaction turns dark purple within the first 4 hours of stirring. The reaction is poured in a sat. aq. NaHCO3 solution and extracted three times with dichloromethane. The combined organics are combined, dried with MgSO4, filtered and concentrated to 192 mg of a purple foam. The crude is purified by LC (230-400 silica gel) eluting with 10% ethyl acetate and 20% dichloromethane in heptane to afford 120 mg of 1-[11-(2-bromoacetyl)-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethanone as a white foam.

Workup

  1. customthe reaction into a homogeneous orange solution
  2. stirringstirred for three days
  3. customturns dark purple within the first 4 hours
  4. stirringof stirring
  5. extractionextracted three times with dichloromethane
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to 192 mg of a purple foam
  9. customThe crude is purified by LC (230-400 silica gel)
  10. washeluting with 10% ethyl acetate and 20% dichloromethane in heptane

Sources & evidence

ORD record
ord-363dfdd946204671b4d4ebce1ef13929
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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