N-bromobutanimide → HCID 58293816, compound

HRID 446738Notes

Reaction equation

HRID 446738 reaction equation
[C:1]([NH:5][C:6]1[C:11]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]4[CH2:25][CH2:24]4)=[C:19]([F:26])[C:18]=3[F:27])[N:15]=[N:14][N:13]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[Br:28]N1C(=O)CCC1=O>C(#N)C>[C:1]([NH:5][C:6]1[C:11]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]4[CH2:25][CH2:24]4)=[C:19]([F:26])[C:18]=3[F:27])[N:15]=[N:14][N:13]=2)=[CH:10][C:9]([Br:28])=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58293789HCID 58293789, compound

Product 1

HCID 58293816HCID 58293816, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 1084 (200 mg, 0.54 mmol) was dissolved in 10 mL of acetonitrile. N-Bromosuccinimide (96 mg, 0.54 mmol) was added to the solution and the reaction mixture was stirred at room temperature for 30 minutes. The reaction was quenched with 1 M Na2S2O3 and the mixture extracted with ethyl acetate. The organice layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford a white solid that was purified by silica gel chromatography to afford 37 mg of N-tert-butyl-5-bromo-3-(1-(4-cyclopropyl-2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine (Compound 1085); MS (M+1)=449.

Workup

  1. customThe reaction was quenched with 1 M Na2S2O3
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialThe organice layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a white solid
  7. customthat was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2086e50088704f8b99dc6a44e3180704
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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