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

HRID 2205935Notes

Reaction equation

HRID 2205935 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH:11]=[O:12])[NH:10][C:4]=2[CH:3]=1.CC1C=CC(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[O:12][CH:25]=[N:24][CH:23]=3)[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 867063216-Bromo-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

Product 1

HCID 867063225-(6-Bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)oxazoleYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

6-Bromo-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde (Preparation 138, 604 mg 2.68 mmole), TOSMIC (1047 mg, 5.37 mmole) and potassium carbonate (759 mg, 5.5 mmole) in methanol (30 mL) was stirred and heated at 65° C. for 110 minutes. The methanol was evaporated and the residue partitioned between ethyl acetate (50 mL) and water (20 mL). The layers were separated and the organic solution was washed with water and brine and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with ethyl acetate to afford the title compound (561 mg, 79%). 1H-NMR (d6-acetone, 500 MHz): δ 7.02 (d, J=0.95 Hz, 1H), 7.60 (t, J=0.95 Hz, 1H), 7.62 (s, 1H), 8.30 (s, 1H), 8.67 (d, J=0.95 Hz, 1H).

Workup

  1. customThe methanol was evaporated
  2. customthe residue partitioned between ethyl acetate (50 mL) and water (20 mL)
  3. customThe layers were separated
  4. washthe organic solution was washed with water and brine
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f77d98356ad54929b1a5ed503f1faf04
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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