Sodium Cyanide → HCID 86658554, compound

HRID 1520199Notes

Reaction equation

HRID 1520199 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22](Br)[N:21]=4)[S:16][C:17]=3[CH3:18])[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[C-:29]#[N:30].[Na+]>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:28]=[CH:27][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[N:21]=[C:22]([C:29]#[N:30])[CH:23]=[CH:24][CH:25]=4)[S:16][C:17]=3[CH3:18])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 86658555HCID 86658555, compound

Product 1

HCID 86658554HCID 86658554, compoundYield 73.4%

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 4 Step 1: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methylthiazol-2-yl)-6-bromopyridin-2-amine (0.94 mmol, 430 mg), NaCN (3.54 mmol, 174 mg), Pd(PPh3)4 (0.42 mmol, 487 mg) and CuI (0.18 mmol, 34 mg) in acetonitrile (22 mL) was microwaved at 180° C. for 6 hours under nitrogen. After evaporation of the solvent, the resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (80:20) as eluent to afford 6-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methylthiazol-2-ylamino)picolinonitrile (0.69 mmol, 277 mg, 73%).

Workup

  1. customAfter evaporation of the solvent
  2. customthe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-8600a746fbc644b5acdd25bc9f1b82c8
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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