Sulfuric Acid → HCID 68108974, compound

HRID 1623858Notes

Reaction equation

HRID 1623858 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][C:12]=2[C:13]([NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:28][Mg]Br.S(=O)(=O)(O)O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[CH:25]=[CH:24][C:23]([CH:26]([OH:27])[CH3:28])=[CH:22][C:12]=2[C:13]([NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 86668212HCID 86668212, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 68108974HCID 68108974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{[(3,4-difluorophenyl)methyl]oxy}-5-formyl-N-3-pyridinylbenzamide (may be prepared as described in Example 80; 100 mg, 0.27 mmol) in tetrahydrofuran (5 ml) was cooled to 0° C. and methylmagnesium bromide (0.18 ml, 0.54 mmol) was added. The mixture was allowed to warm to room temperature and stirred overnight. An additional 3 eq of methylmagnesium bromide was added and the mixture was stirred at room temperature. 5 ml of 1M aqueous sulphuric acid was then added. After stirring for 30 min the mixture was extracted with ethyl acetate (3×10 ml). The organics were combined, evaporated under reduced pressure and the residue was purified by MDAP to yield the title compound. 48 mg.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. stirringAfter stirring for 30 min the mixture
  3. extractionwas extracted with ethyl acetate (3×10 ml)
  4. customevaporated under reduced pressure
  5. customthe residue was purified by MDAP

Sources & evidence

ORD record
ord-0f3612a87486416f877f77f3225f8e9c
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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