Methyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 21898767, compound

HRID 719563Notes

Reaction equation

HRID 719563 reaction equation
[CH2:1]([C:5]1[N:9]=[C:8]([CH3:10])[NH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([O:27]C)=[O:26])=[CH:15][CH:14]=1>>[CH2:1]([C:5]1[N:9]=[C:8]([CH3:10])[N:7]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:25]([OH:27])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 21899050HCID 21899050, compound

Product 1

HCID 21898767HCID 21898767, compoundYield 8.7%

Procedure

Following General Procedure A, 1.0 g (7.2 mmol) of 3-butyl-5-methyl-1H-1,2,4-triazole was reacted with 2.89 g (9.5 mmol) of the alkylating reagent prepared in step 1 of Example 1. Hydrolysis of the slower moving isomer provided 220 mg of 4′-[(3-butyl-5-methyl-1H-1,2,4-triazol-1-yl)methyl][1,1′-biphenyl]-2-carboxylic acid as a colorless solid: NMR (DMSO-d6) δ 0.88 (t, J=7 Hz, 3H), 1.25–1.38 (m, 2H), 1.54–1.67 (m, 2H), 2.39 (s, 3H), 2.54 (t, J=8 Hz, 2H), 5.32 (s, 2H), 7.21 (d, J=8 Hz, 2H), 7.32 (d, J=8 Hz, 2H), 7.36 (dd, J=8 and 2 Hz, 1H), 7.46 (dt, J=8 and 2 Hz, 1H), 7.56 (dt, J=8 and 2 Hz, 1H), 7.72 (dd, J=8 and 2 Hz, 1H).

Workup

  1. customHydrolysis of the

Sources & evidence

ORD record
ord-235d63824e1a47d4927e191442981f3e
Source dataset
uspto-grants-2006_11
Patent number
US07132437B2

Reaction notes

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