4-Carboxyphenylboronic Acid → HCID 21833761, compound

HRID 1741080Notes

Reaction equation

HRID 1741080 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][OH:14])[O:10][N:9]=2)=[CH:4][C:3]=1C.B([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)(O)O>>[OH:14][CH2:13][C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)=[CH:7][CH:6]=2)[N:12]=1

Participants

3

Reactant 2

HCID 3121834-Carboxyphenylboronic AcidHCID 21833845HCID 21833845, compound

Product 1

HCID 21833761HCID 21833761, compound

Procedure

3-(4-Bromo-3-methylphenyl)-1,2,4-oxadiazol-5-ylmethanol (EP 0533268 A1) (1.0 g, 3.7 mmol) was reacted with 4-boronobenzoic acid using similar conditions to Description 11 to afford 4'-(5-hydroxymethyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid. This was dissolved in methanol (70 ml), treated with conc. sulphuric acid (2 ml) and heated under reflux for 4 hours. The solution was concentrated in vacuo and the residue basified with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound (0.76 g, 68%).

Sources & evidence

ORD record
ord-f6b658589f67415caf65fe771824fa1e
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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