Tetrahydrofuran → HCID 66816575, compound

HRID 1697097Notes

Reaction equation

HRID 1697097 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:3]=1.[CH2:21]1[CH2:25]O[CH2:23][CH2:22]1>>[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH2:23][CH2:22][C:21]2[CH:25]=[CH:4][CH:3]=[CH:2][CH:13]=2)=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 71530104HCID 71530104, compound

Product 1

HCID 66816575HCID 66816575, compound

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-fluoro-N-methoxy-N-methyl-2-phenylamino-benzamide (10 g) in THF (80 mL) was slowly added phenethyl-MgBr (91.2 mL, 1 M in THF), and the mixture stirred at 0° C. for 30 min, followed by 1 h at RT. The reaction mixture was then quenched with NH4Cl (sat'd aq), extracted with EtOAc, and chromatographed (0-40% EtOAc/DCM) to provide 1-(4-fluoro-2-phenylamino-phenyl)-3-phenyl-propan-1-one (11.34 g) as a yellow solid.

Workup

  1. customTo a 0° C.
  2. waitfollowed by 1 h at RT
  3. customThe reaction mixture was then quenched with NH4Cl (sat'd aq)
  4. extractionextracted with EtOAc
  5. customchromatographed (0-40% EtOAc/DCM)

Sources & evidence

ORD record
ord-adfd13894659483782a03694bab82ec1
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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