Tetrabutylammonium Fluoride → 2-[4-hydroxyphenyl]-1-cyclohexyl-5-(2H-tetrazol-5-yl)-1H-benzimidazole

HRID 392969Notes

Reaction equation

HRID 392969 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:26]=[CH:27][C:28]([C:30]4[N:31]=[N:32][NH:33][N:34]=4)=[CH:29][C:17]=3[N:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:18]3[CH:26]=[CH:27][C:28]([C:30]4[N:31]=[N:32][NH:33][N:34]=4)=[CH:29][C:17]=3[N:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 226608122-[4-(tert-Butyldimethylsilyoxy)phenyl]-1-cyclohexyl-5-(1H-tetrazol-5-yl)-1H-benzimidazole

Product 1

HCID 1356740942-[4-hydroxyphenyl]-1-cyclohexyl-5-(2H-tetrazol-5-yl)-1H-benzimidazoleYield 210.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 31 (2.65 g, 3.3 mmol) was added to tetrabutylammonium fluoride (17.5 mL of a 1.0 N solution in THF, 17.5 mmol) at rt. The suspension was shaken for 66 h and was filtered. The resin was washed and dried as described in the preceding experiment to afford resin bound 2-[4-hydroxyphenyl]-1-cyclohexyl-5-(2H-tetrazol-5-yl)-1H-benzimidazole (2.5 g).

Workup

  1. filtrationwas filtered
  2. washThe resin was washed
  3. customdried

Sources & evidence

ORD record
ord-d5735cff798c4e5681ff03ee7308c52a
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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