Hydrochloric Acid → HCID 11280762, compound

HRID 2104488Notes

Reaction equation

HRID 2104488 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.CON(C)[C:17]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:26][CH:25]=[CH:24][C:23]=2[C:35]([F:38])([F:37])[F:36])=[O:18].Cl>C1COCC1.CO>[CH3:8][C:4]1[CH:3]=[C:2]([C:17]([C:19]2[CH:20]=[N:21][C:22]3[C:27]([C:28]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][CH:25]=[CH:24][C:23]=3[C:35]([F:38])([F:37])[F:36])=[O:18])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115603-BromotolueneHCID 86598745HCID 86598745, compoundHCID 178418339Butyllithium

Product 1

HCID 11280762HCID 11280762, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

3-Bromotoluene (0.078 mL, 0.64 mmol) was taken into THF (3 mL) and cooled to −78° C. Next, BuLi (0.32 mL of a 2.0 M Solution, 0.64 mmol) was added dropwise and then stirred for 30 minutes. Next, N-methoxy-N-methyl-4-phenyl-8-(trifluoromethyl)quinoline-3-carboxamide (0.231 g, 0.64 mmol) in THF (2 mL) was added quickly via syringe and allowed to stir overnight. MeOH and 2 N HCl were added and stirred for 5 minutes. Then the mixture was extracted with ethyl acetate and dried over magnesium sulfate and concentrated. The resulting material was purified via column chromatography using 10% ethyl acetate in hexane as the eluent to afford 0.060 g of desired product as an off white solid. MS (ESI) m/z 392 ([M+H]+); Anal. Calcd. for C24H16F3NO: C, 73.65; H, 4.12; N, 3.58. Found: C, 73.34; H, 4.08; N, 3.31.

Workup

  1. stirringto stir overnight
  2. stirringstirred for 5 minutes
  3. extractionThen the mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting material was purified via column chromatography

Sources & evidence

ORD record
ord-74a3990811d3482f93f3769275131c8e
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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