HCID 10196880, compound → HCID 58804052, compound

HRID 349276Notes

Reaction equation

HRID 349276 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]([C:20]2[C:21]([CH:32]=[O:33])=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:19])[N:9]=[N:8]1.[CH3:43][Mg]Br>C1COCC1.C(Cl)Cl>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]([C:20]2[C:21]([CH:32]([OH:33])[CH3:43])=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:19])[N:9]=[N:8]1

Participants

5

Reactant 2

HCID 10196880HCID 10196880, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58804052HCID 58804052, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazole-4-carbonyl]-5-(2-chloro-phenyl)-isoxazole-3-carbaldehyde (75 mg, 0.12 mmol) in THF (0.6 mL) at −78° C. under N2, add methylmagnesium bromide (120 μL, 3.0 M in Et2O). Allow the reaction to warm to 0° C. and stir for two h., then quench the reaction with a saturated solution of NH4Cl (1 mL). Dilute the mixture with CH2Cl2 (1 mL), wash with H2O (1 mL) and brine (1 mL). Pass the organic layer through a Varian ChemElute® drying cartridge and concentrate. Purify the residue by chromatography on silica gel using a gradient of 10:1 Hex/EtOAc to 2:1 Hex/EtOAc to afford the title compound (4.3 mg, 6%). MS/ES (M+1)=620.9.

Workup

  1. customthe reaction
  2. customquench
  3. customthe reaction with a saturated solution of NH4Cl (1 mL)
  4. washwash with H2O (1 mL) and brine (1 mL)
  5. customPass the organic layer through a Varian ChemElute® drying cartridge
  6. concentrationconcentrate
  7. customPurify the residue by chromatography on silica gel using a gradient of 10:1 Hex/EtOAc to 2:1 Hex/EtOAc

Sources & evidence

ORD record
ord-608ae833644144aaa32a35ea2f2d7226
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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