Cesium carbonate → HCID 57845457, compound

HRID 734425Notes

Reaction equation

HRID 734425 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18]Br)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5].[CH2:21]([C:23]1[N:24]=[C:25]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([O:35][CH3:36])[CH:29]=2)[O:26][CH:27]=1)[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:20])[CH:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][O:34][C:31]3[CH:32]=[CH:33][C:28]([C:25]4[O:26][CH:27]=[C:23]([CH2:21][CH3:22])[N:24]=4)=[CH:29][C:30]=3[O:35][CH3:36])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 57845500HCID 57845500, compoundHCID 135974501HCID 135974501, compound

Product 1

HCID 57845457HCID 57845457, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

2-[5-(3-Bromo-propoxy)-indol-1-yl]-propionic acid methyl ester (Example 48, 170.20 mg, 0.50 mmol) and 4-(4-ethyl-oxazol-2-yl)-2-methoxy-phenol (Example 39, 109.68 mg, 0.50 mmol) were dissolved in DMF (2 mL) at rt. Cesium carbonate (244.5 mg, 0.75 mmol) was added to the solution, followed by three drops of water. The mixture was stirred at rt for 17 h. The crude reaction mixture was filtered and purified by HPLC. The desired product was isolated as a white solid (143.8 mg, 60.1%). LC/MS m/z 479.3 (M+H)+; RT 3.59 min. 1H NMR (400 MHz, CD2Cl2) δ 7.58 (d, 1H), 7.56 (s, 1H), 7.41 (m, 1H), 7.24 (d, 1H), 7.19 (d, 1H), 7.11 (d, 1H), 7.00 (d, 1H), 6.88 (dd, 1H), 6.46 (d, 1H), 5.11 (q, 1H), 4.28 (t, 2H), 4.22 (t, 2H), 3.93 (s, 3H), 3.71 (s, 3H), 2.61 (q, 2H), 2.34 (m, 2H), 1.82 (d, 3H), 1.29 (t, 3H).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-c4445feef0504bc8ab29e0e0757d8a3d
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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