Dimethylformamide → 2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde

HRID 906387Notes

Reaction equation

HRID 906387 reaction equation
O=P(Cl)(Cl)Cl.[CH:6]([C:9]1[NH:19][C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[CH:10]=1)([CH3:8])[CH3:7].CN([CH:23]=[O:24])C>>[CH:6]([C:9]1[NH:19][C:12]2=[CH:13][N:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:11]2[C:10]=1[CH:23]=[O:24])([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 446084472-Isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine2×

Product 1

HCID 446084482-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde

Conditions

Temperature
90 °C

Procedure

POCl3 (1.1 ml, 12.5 mmol) was added to anhydrous DMF (10 ml) at 0° C. slowly and stirred for 0.5 h. This was added to a solution of 2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine (Compound 5, 468 mg, 2.5 mmol) in anhydrous DMF (15 ml) at room temperature. The mixture was then heated to 90° C. for 2 h and cooled to room temperature, quenched cautiously with aqueous Na2CO3, extracted with EtOAc (×4). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound as beige solid.

Workup

  1. temperaturecooled to room temperature
  2. customquenched cautiously with aqueous Na2CO3
  3. extractionextracted with EtOAc (×4)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-a10a436c799b4267acff1e90d011ab73
Source dataset
uspto-grants-2011_09
Patent number
US08012992B2

Reaction notes

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