Quiflapon → 3-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropanol

HRID 2210558Notes

Reaction equation

HRID 2210558 reaction equation
[CH3:1][C:2]([CH3:41])([S:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[CH:12]=2)[N:7]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:6]=1[CH2:34][C:35]([CH3:40])([CH3:39])[C:36](O)=[O:37])[CH3:3]>C1COCC1>[CH3:3][C:2]([CH3:41])([S:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[CH:12]=2)[N:7]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:6]=1[CH2:34][C:35]([CH3:40])([CH3:39])[CH2:36][OH:37])[CH3:1]

Participants

3

Reactant 1

HCID 60923Quiflapon

Product 1

HCID 193790463-[3-(1,1-Dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropanolYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropionic acid (2.57 g, 4.4 mmol) in THF (20 mls) was added borane dimethyl sulfide complex (1.06 g, 14.0 mmol) dropwise. Upon completion of addition, the reaction was stirred for 18 hrs. It was then quenched slowly and dropwise with aqueous sat'd NaHCO3 (30 mls). The THF was stripped off in vacuo and the aqueous residue was extracted with ethylacetate (3×50 mls). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 1:1) to afford 1.82 g (72%) of 3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropanol as a white foam.

Workup

  1. additionUpon completion of addition
  2. customIt was then quenched slowly and dropwise with aqueous sat'd NaHCO3 (30 mls)
  3. extractionthe aqueous residue was extracted with ethylacetate (3×50 mls)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 1:1)

Sources & evidence

ORD record
ord-e1269ad4b1e1441bb17a43df14655fd9
Source dataset
uspto-grants-1995_10
Patent number
US05459150

Reaction notes

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