Cesium carbonate → HCID 57845510, compound

HRID 2424966Notes

Reaction equation

HRID 2424966 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].[CH2:19]([O:21][C:22](=[O:38])[CH2:23][N:24]1[C:32]2[C:27](=[CH:28][C:29]([O:33][CH2:34][CH2:35][CH2:36]Br)=[CH:30][CH:31]=2)[CH:26]=[CH:25]1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:19][O:21][C:22](=[O:38])[CH2:23][N:24]1[C:32]2[C:27](=[CH:28][C:29]([O:33][CH2:34][CH2:35][CH2:36][O:16][C:13]3[CH:14]=[CH:15][C:10]([C:7]4[S:8][CH:9]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[N:6]=4)=[CH:11][C:12]=3[O:17][CH3:18])=[CH:30][CH:31]=2)[CH:26]=[CH:25]1

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-9c0bcd63ce7b4e8d8dc081eb1d519027
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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