Sodium Carbonate → HCID 178518340, compound

HRID 2236853Notes

Reaction equation

HRID 2236853 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:26][CH2:25][CH2:24][NH:23]2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].Br[CH:34]([OH:36])[CH3:35]>C1COCC1>[OH:36][CH2:34][CH2:35][N:23]1[CH2:24][CH2:25][CH2:26][CH:22]1[C:19]1[CH:20]=[CH:21][C:16]([NH:15][CH:14]=[C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=3)[C:8](=[O:12])[NH:7][C:6]2=[O:13])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 14202443Ethanol, 1-bromo-HCID 178518339HCID 178518339, compound

Product 1

HCID 178518340HCID 178518340, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Iodo-4-[(4-pyrrolidin-2-yl-phenylamino)-methylene]-4H-isoquinoline-1,3-dione (250 mg, 0.54 mmol) and Na2CO3 (2.0 g, 18.9 mmol) in THF (10 mL) is heated to reflux and bromoethanol (0.15 mL) is added every 45 min for 4 hours. The resulting mixture is then allowed to reflux overnight. After TLC suggested no starting material left, the THF is removed and after an aqueous work up, the desired product is isolated through chromatography (75 mg, 28%). MS (ESI): 504.0 (M+1)+1.

Workup

  1. temperatureto reflux
  2. temperatureto reflux overnight
  3. waitleft
  4. customthe THF is removed

Sources & evidence

ORD record
ord-81a1dfdc35c547d9b24118fe56b70e71
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…