Sodium Cyanide → HCID 67207569, compound

HRID 1253461Notes

Reaction equation

HRID 1253461 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[C:7]([O:17][CH3:18])[C:6]=12.[C-:19]#[N:20].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I.C(#N)C>[CH3:18][O:17][C:7]1[C:6]2[N:5]([N:4]=[CH:3][C:2]=2[C:19]#[N:20])[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=1

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 67374188HCID 67374188, compound

Product 1

HCID 67207569HCID 67207569, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

3-iodo-4-methoxy-6-phenylpyrazolo[1,5-a]pyridine (25.0 mg, 0.071 mmol), sodium cyanide (7.0 mg, 0.14 mmol), tetrakis(triphenylphosphine)palladium (0) (4.1 mg, 0.004 mmol), and copper (I) iodide (1.4 mg, 0.007 mmol) were added to a dry flask. Acetonitrile (2 ml) was added and the mixture was sparged with argon for 3 minutes, then heated to 65° C. After 16 h, the reaction mixture cooled and purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give 4-methoxy-6-phenylpyrazolo[1,5-a]pyridine-3-carbonitrile. 1H NMR (600 MHz, DMSO-d6) δ 8.66 (d, 1H); 8.58 (s, 1H); 7.82 (d, 2H); 7.49 (d, 2H); 7.41 (m, 1H); 7.31 (s, 1H); 4.08 (s, 3H). LRMS (ESI) calculated for C15H12N3O [M+H]+, 250.1; found 250.0.

Workup

  1. customthe mixture was sparged with argon for 3 minutes
  2. temperaturethe reaction mixture cooled
  3. custompurified by preparative HPLC Reverse phase (C-18)
  4. washeluting with acetonitrile/water+0.05% TFA

Sources & evidence

ORD record
ord-3c9847cf688e4cd7a1b518d367bb8b34
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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