N-bromobutanimide → HCID 69708076, compound

HRID 22789Notes

Reaction equation

HRID 22789 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[CH:16][C:15]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]3[CH2:25][CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH:12]3[C:11]=2[CH:10]=1.[Br:36]N1C(=O)CCC1=O>CN(C=O)C>[Br:36][C:16]1[C:15]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]3[CH2:25][CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH:12]3[C:11]=2[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69709487HCID 69709487, compound

Product 1

HCID 69708076HCID 69708076, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dry 25 mL round bottom flask was charged with di(tert-butyl) 8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro-1H-pyrido[4,3-b]indole-2,5-dicarboxylate (0.38 g, 0.74 mmol), DMF (10 mL), N-bromosuccinimide (0.21 g, 1.11 mmol), and stirred at ambient temperature for 18 hours. The reaction was concentrated under high vacuum to remove DMF and partitioned between water and ethyl acetate (2X). The organics were combined, dried with MgSO4, filtered and concentrated to give 461 mg of a crude orange brown oil. Purification of the crude on a 40 gram silica Biotage column using 10% ethyl acetate in heptane gave 217 mg (50%) of di(tert-butyl) 6-bromo-8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro-1H-pyrido[4,3-b]indole-2,5-dicarboxylate as a pale yellow foam.

Workup

  1. concentrationThe reaction was concentrated under high vacuum
  2. customto remove DMF
  3. custompartitioned between water and ethyl acetate (2X)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 461 mg of a crude orange brown oil
  8. customPurification of the crude on a 40 gram silica Biotage column

Sources & evidence

ORD record
ord-a604a07adb6c49008b2d94d2caedc081
Source dataset
uspto-grants-2005_02
Patent number
US06849640B2

Reaction notes

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