Cyclohexane → HCID 178506019, compound

HRID 2266643Notes

Reaction equation

HRID 2266643 reaction equation
[F:1][C:2]1[N:6](COCC[Si](C)(C)C)[CH:5]=[N:4][C:3]=1[CH2:15][N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1CCCCC1>O1CCCC1>[F:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:15][N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 2724141Tetrabutylammonium FluorideHCID 59599682HCID 59599682, compound

Product 1

HCID 178506019HCID 178506019, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-[5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-ylmethyl]-1,2,3,4-tetrahydroquinoline (103 mg) at room temperature in tetrahydrofuran (THF) (5 ml) under an argon atmosphere was added tetra-n-butylammonium fluoride (TBAF) (1.1 ml; 1 M solution in THF). The mixture was heated to 60° C. and stirring at that temperature was continued for 20 minutes, then the mixture was adsorbed directly on silica gel. The crude product was isolated by column chromatography (silica gel; gradient: cyclohexane→ethyl acetate) to give 1-(5-fluoro-1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (32 mg) as light yellow solid. (MS (ISP): 232.1 ([M+H]+).

Sources & evidence

ORD record
ord-8e4a9d02db5b4832b069bf7568e57b78
Source dataset
uspto-grants-2010_12
Patent number
US07858652B2

Reaction notes

Loading…