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(2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone → 1-(2,4-Dichloro-3-phenylquinolin-6-yl)-2-methyl-1-(1-methyl-1H-imidazol-5-yl)propan-1-ol

HRID 526855
Notes
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Reaction equation

HRID 526855 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Cl:6][C:7]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([Cl:23])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:24]([C:26]3[N:30]([CH3:31])[CH:29]=[N:28][CH:27]=3)=[O:25])[CH:13]=2)[N:8]=1>C1COCC1>[Cl:6][C:7]1[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:15]([Cl:23])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:24]([C:26]3[N:30]([CH3:31])[CH:29]=[N:28][CH:27]=3)([OH:25])[CH:1]([CH3:3])[CH3:2])[CH:13]=2)[N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 118006377(2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone2×HCID 178418918HCID 178418918, compound

Product 1

HCID 916691921-(2,4-Dichloro-3-phenylquinolin-6-yl)-2-methyl-1-(1-methyl-1H-imidazol-5-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Isopropylmagnesium chloride (2.0 M in THF, 0.056 mL, 0.11 mmol) was added dropwise to a solution of (2,4-dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone (35 mg, 0.092 mmol, Intermediate 2: step b) in THF (1 mL) at 0° C. The mixture was stirred at 0° C. for 5 minutes, then the ice bath was removed and the mixture was stirred for 25 minutes. The reaction was quenched by the addition of saturated aqueous NH4Cl and was diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated to dryness. The residue was purified by RP-HPLC (10-90% CH3CN—H2O, 0.1% TFA), then was converted to the free base (saturated aqueous NaHCO3/DCM extraction) and re-purified by flash column chromatography (silica gel, 25-70% acetone-EtOAc) to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 7.99 (d, J=8.80 Hz, 1H), 7.62 (d, J=8.80 Hz, 1H), 7.46-7.57 (m, 3H), 7.32-7.39 (m, 2H), 7.28-7.32 (m, 1H), 7.18-7.25 (m, 1H), 3.29 (s, 3H), 2.65-2.76 (m, 1H), 1.24 (d, J=6.60 Hz, 3H), 0.72 (d, J=6.85 Hz, 3H); MS m/e 426.1 (M+H)+.

Workup

  1. customthe ice bath was removed
  2. stirringthe mixture was stirred for 25 minutes
  3. customThe reaction was quenched by the addition of saturated aqueous NH4Cl
  4. additionwas diluted with water
  5. extractionThe mixture was extracted three times with EtOAc
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by RP-HPLC (10-90% CH3CN—H2O, 0.1% TFA)
  10. extractionwas converted to the free base (saturated aqueous NaHCO3/DCM extraction)
  11. customre-purified by flash column chromatography (silica gel, 25-70% acetone-EtOAc)

Sources & evidence

ORD record
ord-8716915b0a0244d2a59ba28d8b9a3219
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346782B2

Reaction notes

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