Dimethylformamide → HCID 178489320, compound

HRID 2234709Notes

Reaction equation

HRID 2234709 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:22]=[CH:21][NH:20][N:19]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.CN(C)C=O.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:22]=[CH:21][NH:20][N:19]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 178489326HCID 178489326, compound

Product 1

HCID 178489320HCID 178489320, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2-Methoxy-phenyl)-5-(1H-pyrazol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (156 mg, 0.350 mmol) was dissolved in methanol (1.0 mL) and dimethylformamide (1.0 mL) and 50% w/v aqueous potassium hydroxide (1.0 mL) was added. After 4 hours, the reaction was quenched by addition of acetic acid (1.0 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organic layers were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 3-(2-methoxy-phenyl)-5-(1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine (18.9 mg, 18.6%). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 3.78 (s, 3H), 6.69 (d, J=2.0 Hz, 1H), 6.99 (dt, J=7.0, J=0.5 Hz, 1H), 7.06 (d, J=7.5 Hz, 1H), 7.23 (dt, J=7.0, J=1.5 Hz, 1H), 7.50 (dd, J=7.5, J=1.5 Hz, 1H), 7.63 (d, J=2.5 Hz, 1H), 7.65 (br s, 1H), 8.29 (d, J=2.0 Hz, 1H), 8.63 (br s, 1H), 11.82 (s, 1H). MS: m/z 291 (M+H+).

Workup

  1. additionwas added
  2. customthe reaction was quenched by addition of acetic acid (1.0 mL)
  3. additionThe mixture was carefully poured into saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried to a residue which
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-a154afbabb0f46bdb0e2d3d824c9a3e6
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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