Cesium carbonate → HCID 57845510, compound

HRID 734422Notes

Reaction equation

HRID 734422 reaction equation
[CH:1]([O:4][C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=2)[S:8][CH:9]=1)([CH3:3])[CH3:2].Br[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][C:34]([O:36][CH2:37]C)=[O:35])[CH:28]=[CH:27]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:1]([O:4][C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[N:29]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH:28]=[CH:27]4)=[C:12]([O:17][CH3:18])[CH:11]=2)[S:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86609269HCID 86609269, compoundHCID 135974500HCID 135974500, compound

Product 1

HCID 57845510HCID 57845510, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(4-isopropoxy-1,3-thiazol-2-yl)-2-methoxy-phenol (Example 37, 269 mg, 1.01 mmol) and ethyl [5-(3-bromopropoxy)-1H-indol-1-yl]acetate (Example 47, 331 mg, 1.01 mmol) in 8 mL DMF (containing 1 v/v % of water), was added cesium carbonate (661 mg, 2.03 mmol). After stirring the reaction mixture for 16 h at rt, DMF was evaporated under reduced pressure. The residue was suspended in ethyl acetate and filtered through a silica gel plug to give 204 mg (39%) of a white solid, which was used in the next step with no further purification.

Workup

  1. customDMF was evaporated under reduced pressure
  2. filtrationfiltered through a silica gel plug

Sources & evidence

ORD record
ord-47037ed27f214dc194c80fe399b7489a
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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