Diethyl Ether → HCID 69426777, compound

HRID 916705Notes

Reaction equation

HRID 916705 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=3)[C:19]#[N:20])[CH:11]=2)=[CH:4][CH:3]=1.[CH3:24][Mg]I.CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:19]([NH2:20])[CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH:11]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 69427553HCID 69427553, compoundHCID 178418373HCID 178418373, compound2×

Product 1

HCID 69426777HCID 69426777, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the nitrile from Step 1 (50 mg, 0.16 mmol) in THF (5 mL) was treated with MeMgI in Et2O (3.0 M, 0.32 mL, 0.96 mmol). A milky solution formed, which was stirred at RT for 30 mins, then further MeMgI was added (1.0 mL, 3 mmol) and stirred for 1 hour. A solution of LiAlH4 in THE (1.0 M, 2.5 mL, 2.5 mmol) was added and stirred at RT for 1 hour. The reaction was quenched by addition of H2O and the solvent evaporated under reduced pressure. The residue was partitioned between CH2Cl2 and H2O, the CH2Cl2 layer was separated and the aqueous layer re-extracted with CH2Cl2. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give crude 1-(3-{5-[2-(4-fluorophenyl)-ethyl]-1-methyl-1H-pyrazol-3-yl}-phenyl)-ethylamine as a yellow gum (50 mg).

Workup

  1. customA milky solution formed
  2. stirringstirred for 1 hour
  3. stirringstirred at RT for 1 hour
  4. customThe reaction was quenched by addition of H2O
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was partitioned between CH2Cl2 and H2O
  7. customthe CH2Cl2 layer was separated
  8. extractionthe aqueous layer re-extracted with CH2Cl2
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2e540fced6af47749624fe74b512cd0f
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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