Ammonium Chloride → (1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)(thiazol-2-yl)-methanol

HRID 1432263Notes

Reaction equation

HRID 1432263 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[F:12][C:13]1[CH:34]=[CH:33][C:16]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][C:23]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:24][CH:25]=3)[CH:20]=[C:19]2[CH:31]=[O:32])=[CH:15][CH:14]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[F:12][C:13]1[CH:34]=[CH:33][C:16]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][C:23]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:24][CH:25]=3)[CH:20]=[C:19]2[CH:31]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[OH:32])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 764302-BromothiazoleHCID 225043741-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 22504451(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)(thiazol-2-yl)-methanolYield 28.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a mixture of 2-bromothiazole (123 mg) and tetrahydrofuran (3.5 ml), 1.61 M n-butyl lithium solution in hexane (0.51 ml) was added at −78° C. and the mixture was stirred for 30 minutes, followed by addition of a solution of 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carbaldehyde (50 mg) obtained in Example 27 (4) in tetrahydrofuran (3.5 ml) at the same temperature, and the mixture was stirred as such for 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, extracted with chloroform, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 18 mg of the desired product as a yellow oil.

Workup

  1. additionwas added at −78° C.
  2. stirringthe mixture was stirred as such for 30 minutes
  3. extractionextracted with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1f24ac8428a4affa5a6823a6e025d62
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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