Tributylamine → HCID 53757548, compound

HRID 2229461Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[C:22](I)[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19].[CH2:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:23]=[C:22]([CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-(2-chloro-4-iodobenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole (1.21 g), 1-hexene (1.12 g), palladium acetate (II) (0.09 g), triphenylphosphine (0.21 g), tri-n-butylamine (1.49 g), and N,N-dimethylformamide (15 ml) was stirred overnight at 60° C. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=1/2) to obtain 1-(2-chloro-4-(1-hexen-1-yl)benzyl)-6-(ethoxycarbonyl)-2-methyl-benzimidazole (0.99 g). In accordance with the method of Production Example 5, this product was immediately converted to the desired compound (0.64 g) containing about 10% of 6-carboxy-1-(2-chloro-4-(1-hexen-2-yl)benzyl)-2-methyl-benzimidazole. This compound was immediately subjected to the next step.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=1/2)

Sources & evidence

ORD record: ord-de86ec98496942e2ae70f5bca4b738e2
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420409B1

Reaction notes

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