Chlorosuccinimide → 5-(6-Bromo-3-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)oxazole

HRID 2205939Notes

Reaction equation

HRID 2205939 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[O:15][CH:14]=[N:13][CH:12]=3)[NH:10][C:4]=2[CH:3]=1.[Cl:16]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([Cl:16])=[C:9]([C:11]3[O:15][CH:14]=[N:13][CH:12]=3)[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 867063225-(6-Bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)oxazole

Product 1

HCID 867063275-(6-Bromo-3-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)oxazoleYield 95.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(6-Bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)oxazole (Preparation 139, 80 mg 0.303 mmole) was dissolved in DMF (0.8 mL) and N-chlorosuccinimide (40.4 mg 0.303 mmole) was added. The reaction was stirred at room temperature for 48 hours. The reaction was diluted with ethyl acetate (20 mL) and washed with water (3×7 mL) and brine. The combined aqueous layers were back-washed with ethyl acetate. The organic layers were dried (MgSO4) and concentrated in vacuo to afford the title compound (86 mg). 1H-NMR (d6-acetone, 500 MHz): 7.66 (d, J=0.95 Hz, 1H), 7.84 (s, 1H), 8.40 (s, 1H), 8.66 (d, J=0.63 Hz, 1H), 11.62 (br s, 1H, NH).

Workup

  1. washwashed with water (3×7 mL) and brine
  2. washThe combined aqueous layers were back-washed with ethyl acetate
  3. dry with materialThe organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dfc321c2dae64b948ede19f984da7ce6
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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