Tetrabutylammonium Fluoride → HCID 57709027, compound

HRID 546981Notes

Reaction equation

HRID 546981 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:61])[CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH2:58][CH3:59])([C:38]3[CH:43]=[CH:42][C:41]([C:44]#[C:45][C:46]4([O:52][Si](C)(C)C)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]4)=[C:40]([CH3:57])[CH:39]=3)[CH2:36][CH3:37])=[CH:31][C:30]=2[CH3:60])[CH:28]=1>O1CCCC1>[CH3:19][O:20][C:21](=[O:61])[CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH2:36][CH3:37])([C:38]3[CH:43]=[CH:42][C:41]([C:44]#[C:45][C:46]4([OH:52])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]4)=[C:40]([CH3:57])[CH:39]=3)[CH2:58][CH3:59])=[CH:31][C:30]=2[CH3:60])[CH:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57709081HCID 57709081, compound

Product 1

HCID 57709027HCID 57709027, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.075 mL) was added to [5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclohexylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester (Example 99-(1); 37.3 mg, 0.0625 mmol), and the mixture was stirred for two hours. The reaction mixture was purified by silica gel chromatography (45 to 50% ethyl acetate/hexane) to give the title compound (12.7 mg, 38%).

Workup

  1. customThe reaction mixture was purified by silica gel chromatography (45 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ad00109751304329888e33a17591a0c1
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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