Tetrahydrofuran toluene → HCID 178458170, compound

HRID 2252252Notes

Reaction equation

HRID 2252252 reaction equation
[I:1][C:2]1[C:3]2[CH2:13]C3C(=CC=C(C(OC)=O)C=3)C=2[NH:5][N:6]=1.[CH3:18][Mg+].[Br-].[CH2:21]1[CH2:25][O:24]CC1.[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[I:1][C:2]1[C:3]2[CH2:13][C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:25]([OH:24])([CH3:21])[CH3:18])[CH:30]=3)[C:32]=2[NH:5][N:6]=1

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 178418689HCID 178418689, compoundHCID 178497097HCID 178497097, compound

Product 1

HCID 178458170HCID 178458170, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 236B (1 g, 2.94 mmol) in THF (145 mL) was dropwise added 1.4 M MeMgBr in THF-toluene (8.4 mL, 11.76 mmol). The reaction mixture was slowly warmed to room temperature, stirred for 24 hours, quenched with aqueous NH4Cl, and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 50% ethyl acetate in hexane. The title compound (700 mg) was obtained at 70% yield. MS (DCI/NH3) m/z: 340.95 (M+H)+. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.44 (s, 6H) 3.48 (s, 2H) 5.02 (s, 1H) 7.44 (dd, J=7.80, 1.25 Hz, 1H) 7.48 (m, 1H) 7.65 (s, 1H).

Workup

  1. customquenched with aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1a28d1d66fd94c79a0d3486b934d46d0
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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