Water → HCID 58706888, compound

HRID 1716531Notes

Reaction equation

HRID 1716531 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([CH:20]=[O:21])=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.O.O1CCC[CH2:24]1>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([CH:20]([OH:21])[CH3:24])=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 58706488HCID 58706488, compound

Product 1

HCID 58706888HCID 58706888, compoundYield 62%

Procedure

3M-Methylmagnesium bromide ether solution (0.19 ml, 0.57 mmol) was added to a solution of 5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiophene-2-carboaldehyde (70 mg, 0.24 mmol) in tetrahydrofuran (4 ml) cooled with ice, and after that the mixture was stirred at room temperature for 3 hours in an Ar stream. Water was added to the reaction solution and the solution was extracted with ethyl acetate and the organic layer was washed with a saturated brine and dried over anhydrous magnesium sulfate. Subsequently, the residue obtained by concentration in vacuo was washed with isopropyl ether, dried in vacuo and the title compound (46 mg, 62%) was obtained.

Workup

  1. temperaturecooled with ice
  2. extractionthe solution was extracted with ethyl acetate
  3. washthe organic layer was washed with a saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSubsequently, the residue obtained by concentration in vacuo
  6. washwas washed with isopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-85e510c895594e2e9fab0fcc38408109
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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