Methyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 21898456, compound

HRID 719562Notes

Reaction equation

HRID 719562 reaction equation
[CH2:1]([C:3]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH3:11])[NH:5][N:4]=1)[CH3:2].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([O:28]C)=[O:27])=[CH:16][CH:15]=1>>[CH2:1]([C:3]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH3:11])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:21]([C:26]([OH:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)[N:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 21898375HCID 21898375, compound

Product 1

HCID 21898456HCID 21898456, compoundYield 10.1%

Procedure

Following General Procedure A, 1.0 g (6.0 mmol) of 3-ethyl-5-butyl-1H-1,2,4-triazole was reacted with 2.41 g (7.9 mmol) of the alkylating reagent prepared in step 1 of Example 1. Hydrolysis of the faster moving isomer provided 220 mg of 4′-[(3-ethyl-5-butyl-1H-1,2,4-triazol-1-yl)methyl][1,1′-biphenyl]-2-carboxylic acid as a colorless solid: NMR (DMSO-d6) δ 0.85 (t, J=7 Hz, 3H), 1.19 (t, J=7 Hz, 3H), 1.27–1.38 (m, 2H), 1.52–1.63 (m, 2H), 2.59 (q, J=7 Hz, 2H), 2.74 (t, J=7 Hz, 2H), 5.35 (s, 2H), 7.21 (d, J=8 Hz, 2H), 7.31 (d, J=8 Hz, 2H), 7.35 (dd, J=8 and 2 Hz, 1H), 7.48 (dt, J=8 and 2 Hz, 1H), 7.57 (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-a874f47328d54c969dbe9320da888080
Source dataset
uspto-grants-2006_11
Patent number
US07132437B2

Reaction notes

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