1,2-Dimethoxyethane → HCID 67372393, compound

HRID 1678531Notes

Reaction equation

HRID 1678531 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)=[O:6].C([O:28][C:29]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)=[O:30])C.COCCOC.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:25][O:24][C:23]1[CH:22]=[CH:21][C:4]([C:5](=[O:6])[NH:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:3][C:2]=1[C:34]1[CH:35]=[CH:36][C:31]([C:29]([OH:30])=[O:28])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 4508198HCID 4508198, compound

Product 1

HCID 67372393HCID 67372393, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-Bromo-4-methoxy-N-[4-(4-methyl-piperazin-1-yl)-phenyl]-benzamide (748 mg) and 4-(ethoxycarbonyl)-phenyl boronic acid (538 mg) in 2:1 DME:water (15 ml) containing cesium carbonate (1.21 mg) and tetrakis(triphenylphosphine)palladium0 (220 mg) was heated to reflux for 18 h. The mixture was cooled and then evaporated. The residue was then stirred in ethanol (8 ml) and 2M NaOH (4 ml) at room temp for 16 h. The ethanol was then evaporated and the residue acidified with 2M HCl. The resulting solid was collected by filtration and dried (528 mg)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. temperatureThe mixture was cooled
  4. customevaporated
  5. customThe ethanol was then evaporated
  6. filtrationThe resulting solid was collected by filtration
  7. customdried (528 mg)

Sources & evidence

ORD record
ord-9f51ea11172e41afb1da4cace0306942
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

Loading…