Cesium carbonate → HCID 69099794, compound

HRID 2251570Notes

Reaction equation

HRID 2251570 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:25]=[CH:24][C:12]([CH2:13][NH:14][CH2:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=4)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:32]([O:34][C:35](=[O:40])[C:36](Br)([CH3:38])[CH3:37])[CH3:33].FC(F)(F)OC1C=CC(CBr)=CC=1>C(#N)C>[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:25]=[CH:24][C:12]([CH2:13][NH:14][CH2:15][CH2:16][C:17]4[CH:18]=[CH:19][C:20]([O:23][C:36]([CH3:38])([CH3:37])[C:35]([O:34][CH2:32][CH3:33])=[O:40])=[CH:21][CH:22]=4)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 69099606HCID 69099606, compound

Product 1

HCID 69099794HCID 69099794, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a warm solution of 4-(2-{[4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]amino}ethyl)phenol (0.42 g, 1.25 mmol) in acetonitrile (6 ml) was added Cs2CO3 (1.34 g, 4.11 mmol) followed by ethyl-2-bromoisobutyrate (0.60 mL, 4.09 mmol). The mixture was heated at 80C for 20 h. Upon cooling, the mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (2×25 ml). The combined organic phases were dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (MeOH/EtOAc, 2:98) to yield ethyl 2-[4-(2-{[4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (0.42 g, 74%).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and water
  3. extractionThe aqueous phase was extracted with EtOAc (2×25 ml)
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (MeOH/EtOAc, 2:98)

Sources & evidence

ORD record
ord-ae4ebef932494e22afb54c251699a633
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

Loading…