1-Bromo-2-butanone → ethyl ((1S)-5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2235891Notes

Reaction equation

HRID 2235891 reaction equation
[NH2:1][C:2]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]3)=[C:6]([CH2:30][CH2:31][CH3:32])[CH:5]=1)=[S:3].Br[CH2:34][C:35](=O)[CH2:36][CH3:37]>CCO>[CH2:36]([C:35]1[N:1]=[C:2]([C:4]2[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]4)=[C:6]([CH2:30][CH2:31][CH3:32])[CH:5]=2)[S:3][CH:34]=1)[CH3:37]

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 16110446ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 16110452ethyl ((1S)-5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetateYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (90 mg, 0.2 mmol) (Example 144) and 1-bromo-2-butanone (35.8 mg, 0.24 mmol) in EtOH (anhydrous, 8 mL) was heated at 70° C. for 6 h. The reaction mixture was cooled to rt, and then concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v) 1:2) gave 42 mg (42%) of the title compound as a clear oil. LC-MS: RT=4.85 min; (M+H)+ 508.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v) 1:2)

Sources & evidence

ORD record
ord-751257a0095e4000bcf88380f8c29dad
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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