Water → HCID 23146402, compound

HRID 2378030Notes

Reaction equation

HRID 2378030 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]1[N:9](COCC[Si](C)(C)C)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[S:36][C:35]([CH3:37])=[N:34][C:33]=2[C:38](Cl)=[O:39])=[CH:28][CH:27]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[F:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[S:36][C:35]([CH3:37])=[N:34][C:33]=2[C:38]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[CH2:7][C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:39])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 223241192-Methyl-5-(4-fluorophenyl)thiazole-4-carbonyl chlorideHCID 66967862HCID 66967862, compound

Product 1

HCID 23146402HCID 23146402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(RS)-1-[5-(4-Fluoro-phenyl)2-methyl-thiazol-4-yl]-1-{2-[1-(2-trimethylsilanyl-oxymethyl)-1H-indol-2-ylmethyl]-piperidin-1-yl}-methanone (130 mg) was prepared from (RS)-2-piperidin-2-ylmethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole, D68 (520 mg) and 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carbonyl chloride (512 mg) according to a procedure similar to that for Example 1. A stirring solution of the above amide (125 mg) in dry THF (5 ml) was treated with a solution of tetrabutylammonium fluoride (2.2 mmol) in THF (5 ml). Once tlc indicated the reaction had gone to completion, the reaction mixture was poured into water and the product extracted with ethyl acetate. The combined organics were washed with brine, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (silica gel, 0-100% pentane-ethyl acetate followed by preparative tlc, 40% ethyl acetate-pentane) afforded the title compound as a white solid (2.5 mg).

Workup

  1. extractionthe product extracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a20e1d19bae149778653551496cf7123
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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