Dimethylformamide → (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-1-methyl-1H-pyrrole-2-carboxamide

HRID 1821323Notes

Reaction equation

HRID 1821323 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.S(Cl)(Cl)=O.CN(C=O)C.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH2:36])=[N:20]1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C1COCC1.O.CO>[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)=[O:9])=[N:20]1

Participants

11

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 69001756HCID 69001756, compound

Product 1

HCID 68998430(E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-1-methyl-1H-pyrrole-2-carboxamideYield 69%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1-Methyl-2-pyrrolecarboxylic acid (1.49 g, 11.9 mmol) was dissolved in methylene chloride (12 mL) and the solution was added with thionyl chloride (1.3 mL, 17.85 mmol) and DMF (276 μL, 3.57 mmol) at 0° C., stirred at 40° C. for 2 hours and then the mixture was concentrated. The mixture was dissolved in THF, added with a solution of (E)-2-[2-(1H-indazol-3-yl)vinyl]phenylamine (700 mg, 2.98 mmol) and triethylamine (1.25 mL, 8.93 mmol) in THF (10 mL) at room temperature, stirred at 60° C. for 4 hours. Further, potassium carbonate and methanol (10 mL) were added to the mixture and stirred for a while and then added with water. The precipitated solid was collected by filtration and reslurried with ethanol to obtain Compound 29 (703 mg, 69%).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe mixture was dissolved in THF
  3. stirringstirred at 60° C. for 4 hours
  4. stirringstirred for a while
  5. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-7af7b2b0fc5244779bc8127b41b240f0
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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