Water → HCID 58126992, compound

HRID 1968436Notes

Reaction equation

HRID 1968436 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11].O.[C-:17]#[N:18].[Na+]>CN(C=O)C>[C:17]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])#[N:18]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 16753950HCID 16753950, compound

Product 1

HCID 58126992HCID 58126992, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of example 20 (˜90% pure, 729 mg, 2.46 mmol) in a mixture of DMF:H2O (3 mL:2 mL) and sodium cyanide (362 mg, 7.4 mmol) was stirred at room temperature overnight. The resulting mixture was quenched with saturated NaHCO3 (12 mL) and extracted with ethylacetate (3×30 mL). The extracts were combined and washed with saturated NaCl (2×30 mL) and water (2×30 mL). The organic layer was separated, dried over anhydrous MgSO4 and concentrated under reduced pressure to give the titled product as a colourless oil (503 mg, 85% yield).

Workup

  1. customThe resulting mixture was quenched with saturated NaHCO3 (12 mL)
  2. extractionextracted with ethylacetate (3×30 mL)
  3. washwashed with saturated NaCl (2×30 mL) and water (2×30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a310cb0da51c4e668e79dc421e4e515c
Source dataset
uspto-grants-2013_04
Patent number
US08426405B2

Reaction notes

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