2-Chloro-3-(trifluoromethyl)benzoyl chloride → HCID 90409113, compound

HRID 2177563Notes

Reaction equation

HRID 2177563 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[N:10]=[CH:9]2)=[N:6][CH:7]=1.[Cl:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].[CH3:31][Mg+].[Br-]>C1COCC1.CCOCC>[Cl:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:13]1[CH:14]=[CH:15][C:16]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)[CH:9]=[N:10][C:11]=2[CH:12]1[CH3:31])=[O:21]

Participants

6

Reactant 3

HCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 904095831-(5-Fluoropyridin-2-yl)-1H-imidazo[4,5-c]pyridineHCID 178418689HCID 178418689, compound

Product 1

HCID 90409113HCID 90409113, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of Intermediate 1 (0.70 g, 3.27 mmol) in THF (20 mL) was added Intermediate 12 (0.87 g, 3.60 mmol) dropwise. The reaction was allowed to stir for 1 h then cooled to −78° C. To the cooled solution was added 3M MeMgBr in Et2O (1.31 mL, 3.92 mmoL) and the reaction was let come to room temperature. The mixture was then quenched with 1N NaOH (50 mL) and extracted with EtOAc (3×30 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH (NH3):DCM) gave the title compound (770 mg, 54%). 1H NMR (400 MHz, CDCl3) δ 8.43-8.34 (m, 1H), 7.92-7.73 (m, 2H), 7.70-7.33 (m, 4H), 6.08 (dtd, J=19.7, 11.7, 8.0 Hz, 3H), 1.54 (t, J=7.0 Hz, 3H). MS (ESI): mass calculated for C20H13ClF4N4O, 436.07. m/z found 437.1 [M+H]+.

Workup

  1. customwas let come to room temperature
  2. customThe mixture was then quenched with 1N NaOH (50 mL)
  3. extractionextracted with EtOAc (3×30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f90cd87a42234a698026c8852db31c31
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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