Potassium Cyanide → HCID 86658569, compound

HRID 1520217Notes

Reaction equation

HRID 1520217 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:16][CH:17]=3)[C:10](Cl)=[N:9]2)=[CH:5][CH:4]=1.[C-:28]#[N:29].[K+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:16][CH:17]=3)[C:10]([C:28]#[N:29])=[N:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 86658570HCID 86658570, compound

Product 1

HCID 86658569HCID 86658569, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

According to Scheme 13 Step 1: A solution of N-(4-(1-(4-methoxybenzyl)-3-chloro-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-2-amine (75 μmol, 30 mg), KCN (75 μmol, 4.9 mg), Pd(PPh3)4 (7.5 μmol, 8.7 mg) and CuI (75 μmol, 14.4 mg) in acetonitrile (2 mL) was microwaved at 180° C. for 50 minutes under nitrogen. After evaporation of the solvent, the crude residue was dissolved in AcOEt. The organic phase was washed with a saturated aqueous solution of Na2CO3, was dried over MgSO4, was filtered and was concentrated to yield 1-(4-methoxybenzyl)-4-(2-(pyridin-2-ylamino)thiazol-4-yl)-1H-pyrazole-3-carbonitrile (51 μmol, 20 mg, 68%).

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe crude residue was dissolved in AcOEt
  3. washThe organic phase was washed with a saturated aqueous solution of Na2CO3
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-1310b16c60644a52a763acc0751bb579
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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