Ammonium Chloride → HCID 10047221, compound

HRID 857640Notes

Reaction equation

HRID 857640 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]=[C:21]([CH:26]=[O:27])[CH:22]=[N:23]4)=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1.[CH3:30][Mg]Br.[NH4+].[Cl-]>C1COCC1>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]=[C:21]([CH:26]([OH:27])[CH3:30])[CH:22]=[N:23]4)=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21865045HCID 21865045, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10047221HCID 10047221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 7-{6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yloxy}quinoline-3-carbaldehyde, (Example 60b), (220 mg, 0.56 mmol) in anhydrous THF (10 mL) was magnetically stirred under N2 in a −78° C. bath while methylmagnesium bromide (0.22 mL, 0.66 mmol, 3.0 M in Et2O, Aldrich) was added quickly. The reaction mixture was stirred at −78° C. for 5 min, then treated with satd NH4Cl (5 mL). The bath was removed and the mixture was stirred for 5 min, then diluted with EtOAc (60 mL) and washed with satd NH4Cl (20 mL), water (20 mL), satd NaHCO3 (20 mL), satd NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (gradient: 60A-85% EtOAc in hexanes) provided the title compound as an off-white solid. Mp: 156–157° C. MS (ESI, pos. ion.) m/z: 412 (M+1). Anal. Calcd for C22H16F3N3O2: C, 64.23; H, 3.92; N, 10.21; F, 13.85. Found: C, 63.99; H, 4.05; N, 10.01; F, 13.63.

Workup

  1. additionwas added quickly
  2. customThe bath was removed
  3. stirringthe mixture was stirred for 5 min
  4. additiondiluted with EtOAc (60 mL)
  5. washwashed with satd NH4Cl (20 mL), water (20 mL), satd NaHCO3 (20 mL), satd NaCl (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customPurification by silica gel chromatography (gradient: 60A-85% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e2b1ebf5145548f5b51c34ef101767d0
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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