Sulfuric Acid → HCID 69053645, compound

HRID 2110990Notes

Reaction equation

HRID 2110990 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[SiH](CC)(CC)CC.[OH-].[Na+]>FC(F)(F)C(O)=O.O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[N:7][CH:6]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 22626666HCID 22626666, compound

Product 1

HCID 69053645HCID 69053645, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(6-Amino-3-pyridinyl)(4-fluorophenyl)methanone (30 mg, 0.138 mmol) was dissolved in 1 ml of trifluoroacetic acid. 16 l of sulfuric acid (2.2 eq) and 50 l of Et3SiH and stirred at ambient temperature for 4 h in a closed vial. The reaction mixture was poured into water, basified with 2N sodium hydroxide and extracted into methylene chloride. Organic extract was washed with water and brine, concentrated and purified by column chromatography on silica (10 g, EtOAc/hexane 1:1) to give 12 mg of desired product (43% yield).

Workup

  1. extractionextracted into methylene chloride
  2. extractionOrganic extract
  3. washwas washed with water and brine
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica (10 g, EtOAc/hexane 1:1)

Sources & evidence

ORD record
ord-d67c42ae3e6b453382097dabbaaad524
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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