HCID 57606110, compound → HCID 57606107, compound

HRID 1409798Notes

Reaction equation

HRID 1409798 reaction equation
CON(C)[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([CH3:16])=[C:14]([C:17]([F:20])([F:19])[F:18])[O:13][N:12]=2)=[CH:7][CH:6]=1.[C:23]([Mg]Br)([CH3:26])([CH3:25])[CH3:24]>>[CH3:24][C:23]([CH3:26])([CH3:25])[C:4]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([CH3:16])=[C:14]([C:17]([F:18])([F:19])[F:20])[O:13][N:12]=2)=[CH:9][CH:10]=1)=[O:21]

Participants

3

Reactant 2

HCID 57606110HCID 57606110, compoundHCID 178418586HCID 178418586, compound

Product 1

HCID 57606107HCID 57606107, compoundYield 9%

Procedure

Prepared from N-Methoxy-N-methyl-4-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-benzamide and tert-butylmagnesium bromide as described in Example 5. Chromatographed on silica gel with EtOAc/hexanes (5%) as eluant to afford product as a colorless solid (53 mg, 9%). 1H NMR (CDCl3) 1.37 (s, 9 H), 2.29 (d, J=1.3, 3 H), 7.68 (d, J=7.9, 2 H), 7.81 (d, J=8.3, 2 H). 19F NMR −63.2. LC/MS 7.42 min, [M+1]+ 312.

Workup

  1. customChromatographed on silica gel with EtOAc/hexanes (5%) as eluant

Sources & evidence

ORD record
ord-79b0360a6d514a54bb2dd27fa9898518
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

Loading…