HCID 11717093, compound → HCID 11559143, compound

HRID 746616Notes

Reaction equation

HRID 746616 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][N:8]([CH3:30])[CH2:9][CH2:10][C:11]1[S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[N:23]=1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:29][O:28][C:24]1[N:23]=[C:22]([C:20]([C:12]2[C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[S:15][C:11]=2[CH2:10][CH2:9][N:8]([CH3:30])[CH3:7])=[CH2:1])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 11717093HCID 11717093, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11559143HCID 11559143, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (8 mL) was added to a mixture of potassium t-butoxide (140 mg, 1.27 mmol) and methyltriphenylphosphonium bromide (0.45 g, 1.27 mmol) under N2 atmosphere. The reaction was stirred for 30 min at room temperature. A solution of [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-(6-methoxy-pyridin-2-yl)-methanone (0.29 g, 0.85 mmol) in THF (8 mL) was added and the reaction was stirred for 1 hour at room temperature. The reaction was quenched by the addition of 0.1N HCl until the pH was <3 and extracted with 0.1N HCl. The aqueous layers were made basic with NH4OH and extracted with EtOAc. The organic layers were washed with water and concentrated in vacuo. Mass triggered preparative HPLC afforded 190 mg of (2-{3-[1-(6-methoxy-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 15-1) as a TFA salt.

Workup

  1. stirringthe reaction was stirred for 1 hour at room temperature
  2. customThe reaction was quenched by the addition of 0.1N HCl until the pH was <3
  3. extractionextracted with 0.1N HCl
  4. extractionextracted with EtOAc
  5. washThe organic layers were washed with water
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a238193389d47f39d16df59521dc562
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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