4-Bromo-3-(methoxymethyl)benzoic acid → Methyl 4-{5-[4-bromo-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

HRID 219950Notes

Reaction equation

HRID 219950 reaction equation
[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=1.[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=O)=[CH:19][C:18]=1[CH2:26][O:27][CH3:28]>C(#N)C>[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]2[O:15][N:14]=[C:2]([C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=3)[N:1]=2)=[CH:19][C:18]=1[CH2:26][O:27][CH3:28]

Participants

4

Reactant 2

HCID 197712294-Bromo-3-(methoxymethyl)benzoic acidHCID 76644654Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate

Product 1

HCID 67528348Methyl 4-{5-[4-bromo-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was obtained following procedure described for example 4, step 1, but starting from Intermediate 1 (0.50 g; 2.36 mmol) and Intermediate 37 (0.64 g; 2.59 mmol). Title compound was isolated after trituration with ACN as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.23 (d, J=2 Hz, 1H), 8.14-8.09 (m, 1H), 8.06-8.02 (m, 1H), 8-7.92 (m, 3H), 4.57 (s, 2H), 3.90 (s, 3H), 3.46 (s, 3H). LC/MS (Method B): 423.1 (M+H)+. HPLC (Method A) Rt 5.91 min (purity: 98.5%).

Sources & evidence

ORD record
ord-c1045c69a4c641a9ae022a383a5b0471
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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