Tetrahydrofuran → HCID 11256967, compound

HRID 884807Notes

Reaction equation

HRID 884807 reaction equation
C1([Mg]Cl)CCCCC1.I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[NH2:16][C:17]1[N:21]([C:22]2[CH:23]=[C:24]([CH:31]=[CH:32][C:33]=2[CH3:34])[C:25]([NH:27][CH:28]2[CH2:30][CH2:29]2)=[O:26])[N:20]=[CH:19][C:18]=1[C:35]#N.C1C[O:40]CC1>>[NH2:16][C:17]1[N:21]([C:22]2[CH:23]=[C:24]([CH:31]=[CH:32][C:33]=2[CH3:34])[C:25]([NH:27][CH:28]2[CH2:30][CH2:29]2)=[O:26])[N:20]=[CH:19][C:18]=1[C:35]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:40]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 2211262-IodopyridineHCID 67024193HCID 67024193, compoundHCID 178478990HCID 178478990, compound

Product 1

HCID 11256967HCID 11256967, compoundYield 33%

Procedure

Cyclohexylmagnesium chloride (5 mL, 2.0 M in Et2O) was added dropwise to the solution of 2-iodopyridine (1.03 g, 5 mmol) in THF (15 mL) at −20° C. The mixture was stirred at this temperature for 20 min before 3-(5-Amino-4-cyano-pyrazol-1-yl)-N-cyclopropyl-4-methyl-benzamide (140 mg, 0.5 mmol) was added, then stirred at room temperature over night. The reaction was quenched by the addition of K2CO3 aqueous solution, then the mixture was extracted with EtOAc and the organic layers washed with water and brine. Purification by column chromatography on silica gel eluted with EtOAc provided the product as a white solid (60 mg, 33%). HPLC (4 minute 10-90 gradient) tR 2.09 min; MS m/z 362.20 [M+H]+.

Workup

  1. additionwas added
  2. customThe reaction was quenched by the addition of K2CO3 aqueous solution
  3. extractionthe mixture was extracted with EtOAc
  4. washthe organic layers washed with water and brine
  5. customPurification by column chromatography on silica gel
  6. washeluted with EtOAc

Sources & evidence

ORD record
ord-55808f9eacb74cd598d09eafa73ce399
Source dataset
uspto-grants-2012_08
Patent number
US08242117B2

Reaction notes

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