N-Methoxy-N-methylbiphenyl-3-carboxamide → Biphenyl-3-yl(3,4,5-trimethoxyphenyl)methanone

HRID 70013Notes

Reaction equation

HRID 70013 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([Mg]Br)[CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28]>C1COCC1>[C:8]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([C:23]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:21]([O:20][CH3:19])[CH:22]=2)=[O:5])[CH:7]=1

Participants

4

Reactant 2

HCID 10377041N-Methoxy-N-methylbiphenyl-3-carboxamideHCID 178492974HCID 178492974, compound

Product 1

HCID 53364048Biphenyl-3-yl(3,4,5-trimethoxyphenyl)methanoneYield 43.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 38a (FIG. 2) (0.174 g, 0.72 mmoL) in 5 mL THF was added a THF solution of 3,4,5-trimethoxyphenylmagnesiumbromide (0.5 N, 1.08 mmol) at 0° C. The mixture was allowed to stir for 30 min and quenched with satd. NH4Cl, extracted with ethyl ether, dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 1a as a white solid (43.8%). NMR (CDCl3) δ 8.02 (t, 1H), 7.84-7.74 (m, 2H), 7.64-7.38 (m, 6H), 7.11 (s, 2H), 3.95 (s, 3H), 3.88 (s, 6H); MS (ESI) m/z 371.1 (M+Na)+.

Workup

  1. customquenched with satd
  2. extractionNH4Cl, extracted with ethyl ether
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cf0db99d9788459ea55381bc6057d1a7
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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