Hydrochloric Acid → HCID 58579532, compound

HRID 1662211Notes

Reaction equation

HRID 1662211 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.C([Li])(C)(C)C.[Br:17][C:18]1[CH:19]=[C:20](/[C:26](/[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:35]=2[C:41]#[N:42])=[N:27]\S(C(C)(C)C)=O)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].Cl.CO>C1COCC1>[Br:17][C:18]1[CH:19]=[C:20]([C:26]2([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=3)[C:34]3[C:35](=[C:36]([F:40])[CH:37]=[CH:38][CH:39]=3)[C:41]([NH2:42])=[N:27]2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 234369504-Bromo-2-(trifluoromethyl)pyridineHCID 58579491(NE)-N-[(3-bromo-4-methoxyphenyl)-(2-cyano-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamideHCID 178418306HCID 178418306, compound

Product 1

HCID 58579532HCID 58579532, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-bromo-2-trifluoromethylpyridine (1.76 g, 7.80 mmol) in THF (2 mL) was added dropwise at −100° C. to t-butyllithium (9.17 mL, 15.59 mmol) in THF (15 mL) followed by the addition of (E)-N-((3-bromo-4-methoxyphenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (3.1 g, 7.09 mmol) in THF (10 mL). The reaction mixture was left on a thawing cooling bath for 1 hour and then allowed to reach room temperature and stirred for 2.5 hours. Hydrochloric acid in methanol (1.25 M, 28.4 mL, 35.4 mmol) was added and the reaction was stirred for 1 hour. Silica powder was added and the mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% 0.1M NH3 in methanol in DCM) to afford the title compound (3.04 g, 89%).

Workup

  1. waitThe reaction mixture was left on a thawing
  2. temperaturecooling bath for 1 hour
  3. customto reach room temperature
  4. stirringthe reaction was stirred for 1 hour
  5. additionSilica powder was added
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (0-10% 0.1M NH3 in methanol in DCM)

Sources & evidence

ORD record
ord-a095c90993e64ef8a02dec7dd0dbca61
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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