N-bromobutanimide → HCID 178424028, compound

HRID 2174014Notes

Reaction equation

HRID 2174014 reaction equation
[CH3:1][C:2]1[C:3]([CH2:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=3[N:14]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.C1C(=O)N([Br:31])C(=O)C1>CN(C=O)C>[Br:31][C:5]1[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([CH3:1])[C:3]=2[CH2:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=3[N:14]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178424030HCID 178424030, compound

Product 1

HCID 178424028HCID 178424028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-((5,7-Dimethyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (Example 58-C) (61 mg, 0.203 mmol) was dissolved in DMF (2 mL) and NBS (40.1 mg, 0.225 mmol) was added at 0° C. and the reaction stirred for 1 hour. The reaction was then quenched with saturated aq. sodium thiosulfate and saturated aq. NaHCO3. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic phase was dried over MgSO4, concentrated and purified by flash column chromatography (0-40% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.33 (br. s., 1H) 11.39 (br. s., 1H) 7.97 (s, 1H) 7.83 (s, 1H) 7.41-7.64 (m, 2H) 6.86 (s, 1H) 4.82 (d, J=4.55 Hz, 2H) 2.43 (s, 3H) 2.21 (s, 3H). HRMS calcd. for C19H15BrN4 (M+H)+ 379.0553. found 379.0557.

Workup

  1. customThe reaction was then quenched with saturated aq. sodium thiosulfate and saturated aq. NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (0-40% EtOAc in heptanes)

Sources & evidence

ORD record
ord-ba30a8d9a28d4665b7cc622788dd4399
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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