Cesium carbonate → HCID 178518298, compound

HRID 2236646Notes

Reaction equation

HRID 2236646 reaction equation
Br[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]([CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:18][CH:17]=1.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]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:17]=[CH:18][C:19]([CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2734357Furan-2-boronic acidHCID 178518259HCID 178518259, compound

Product 1

HCID 178518298HCID 178518298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
150 °C

Procedure

To a suspension of 6-bromo-4-[(4-pyrrolidin-1-ylmethyl-phenylamino)-methylene]-4H-isoquinoline-1,3-dione (40 mg, 0.1 mmol) in N,N-dimethylformamide (1 mL) is added 2-furanboronic acid (11.2 mg, 0.1 mmol), followed by 60 μL of 2M aqueous cesium carbonate and tetrakis triphenylphosphine palladium (6 mg, 0.005 mmol). The reaction mixture is subjected to microwave heating at 150° C. for 100 seconds. The reaction mixture is then diluted to 2 mL with N,N-dimethylformamide and purified by C18 reverse phase HPLC. The pure fractions were combined and concentrated to yield Example 169.

Workup

  1. custompurified by C18 reverse phase HPLC
  2. concentrationconcentrated
  3. customto yield Example 169

Sources & evidence

ORD record
ord-656a6d108fd9446b9b167124d777fdb6
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…