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

HRID 2235859Notes

Reaction equation

HRID 2235859 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH2:16][CH3:17])[N:15]=2)=[CH:7][C:6]=1[CH2:18][CH2:19][CH3:20].[CH2:21]([O:23][C:24](=[O:36])[CH2:25][C@H:26]1[C:34]2[C:29](=[CH:30][C:31]([OH:35])=[CH:32][CH:33]=2)[CH2:28][CH2:27]1)[CH3:22].O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:21]([O:23][C:24](=[O:36])[CH2:25][C@H:26]1[C:34]2[C:29](=[CH:30][C:31]([O:35][CH2:2][CH2:3][O:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[S:12][CH:13]=[C:14]([CH2:16][CH3:17])[N:15]=4)=[CH:7][C:6]=3[CH2:18][CH2:19][CH3:20])=[CH:32][CH:33]=2)[CH2:28][CH2:27]1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 593005482-[4-(2-Bromoethoxy)-3-propylphenyl]-4-ethyl-1,3-thiazole

Product 1

HCID 59300542ethyl ((1S)-5-{2-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]-ethoxy}-2,3-dihydro-1H-inden-1-yl)acetateYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-[4-(2-bromoethoxy)-3-propylphenyl]-4-ethyl-1,3-thiazole (105 mg 0.30 mmol) (Example 34) and ethyl[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (65 mg, 0.30 mmol) (Example 6) in DMF (4 mL, containing 1% v/v of water), was added Cs2CO3 (145 mg, 0.44 mmol), and the mixture was stirred for 24 h at rt. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in EtOAc and filtered. The filtrate was concentrated and purified by silica gel chromatography (gradient: 100% hexane to 1:9 (v/v) EtOAc/hexane) to give 66 mg (41%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 7.72-7.58 (m, 3H), 6.98 (d, 1H), 6.86-6.60 (m, 3H), 4.33-4.28 (br, 2H), 4.28-4.20 (br, 1H), 4.10 (q, 2H), 3.52-3.40 (m, 1H), 2.84 (m, 4H), 2.64 (dd, 1H), 2.58-2.50 (m, 3H), 2.40-2.24 (m, 2H), 1.72-1.50 (m, 3H), 1.26 (t, 3H), 1.20 (t, 3H), 0.84 (t, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography (gradient: 100% hexane to 1:9 (v/v) EtOAc/hexane)

Sources & evidence

ORD record
ord-af86fe3d47f143dd8edf72987af47076
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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