N-Iodosuccinimide → 3-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

HRID 1253455Notes

Reaction equation

HRID 1253455 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][CH:17]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[I:18]N1C(=O)CCC1=O>C(#N)C.ClCCl>[I:18][C:17]1[CH:16]=[N:15][N:5]2[CH:6]=[C:7]([C:9]3[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=3)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=12

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 58404846HCID 58404846, compound

Product 1

HCID 448167683-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (486 mg, 2.13 mmol) was suspended in acetonitrile (30 ml). N-iodosuccinimide (958 mg, 4.26 mmol) was added and the mixture was allowed to stir for 1 h. The reaction mixture was diluted in dichloromethane, washed with water, 1N aqueous sodium hydroxide and brine. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 3-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine as a tan solid. 1H NMR (500 MHz, DMSO-d6) δ 8.67 (s, 1H); 8.28 (s, 1H); 8.01 (s, 1H); 7.92 (1, 1H); 6.89 (s, 1H); 3.96 (s, 3H); 3.85 (s, 3H). LRMS (ESI) calculated for C12H12IN4O [M+H]+, 355.0; found 354.9.

Workup

  1. washwashed with water, 1N aqueous sodium hydroxide and brine
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7f4901e0bcb648b7bc9e5b4559f2495f
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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