2,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid → Methyl 4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-3-fluorobenzoate

HRID 219909Notes

Reaction equation

HRID 219909 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].[NH2:18][C:19](=[N:31]O)[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[F:30]>>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:10][N:31]=[C:19]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=3[F:30])[N:18]=2)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]

Participants

3

Reactant 2

HCID 219373032,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acidHCID 72307476Methyl 4-[amino(hydroxyimino)methyl]-3-fluorobenzoate

Product 1

HCID 67529742Methyl 4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-3-fluorobenzoate

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 3 (113.1 mg; 0.50 mmol; 1 eq.) and Intermediate 2 (106.1 mg; 0.50 mmol; 1 eq.). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5), affording the title compound as a off-white solid. LC/MS (Method A): 403.0 (M+H)+. HPLC (Method A) Rt 6.20 min (Purity: 96.8%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  3. washrinsed with ACN
  4. washrinsed with ACN
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5)

Sources & evidence

ORD record
ord-58d1b9bc56184252b8f9057383d3023d
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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