Cesium carbonate → Ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate

HRID 2189735Notes

Reaction equation

HRID 2189735 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][N:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN1C(=O)N(C)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68320Ethyl 3-bromopropionateHCID 532392355-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazole

Product 1

HCID 59316704Ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

5-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazole (D4) (200 mg) was dissolved in DMPU (2.8 ml) and treated with Cs2CO3 (367 mg) followed by ethyl 3-bromopropionate (145 ul). The resultant mixture was heated to 140° C. in a microwave reactor for 1.5 hours. The reaction mixture was then cooled to RT, evaporated to dryness and dissolved in H2O. This solution was extracted with EtOAc (×3) and the combined extracts washed with brine and evaporated to give the title compound (240 mg) as a brown oil. MS (ES): C23H2335ClN4O4 requires 454; found 455 (MH+).

Workup

  1. customevaporated to dryness
  2. dissolutiondissolved in H2O
  3. extractionThis solution was extracted with EtOAc (×3)
  4. washthe combined extracts washed with brine
  5. customevaporated

Sources & evidence

ORD record
ord-05ca30f0e11b480b8e85c7368d1fca37
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

Loading…