2-(Tributylstannyl)furan → HCID 178518299, compound

HRID 2236855Notes

Reaction equation

HRID 2236855 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][CH:24]2[CH2:28][OH:29])=[CH:18][CH:17]=1.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[Sn](CCCC)(CCCC)CCCC>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]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]([CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[CH2:28][OH:29])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 178518260HCID 178518260, compound

Product 1

HCID 178518299HCID 178518299, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-4-{[4-(2-hydroxymethyl-pyrrolidin-1-ylmethyl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione (130 mg, 0.26 mmol) and 2-furyltributyltin (270 mg, 0.76 mmol) and PdCl2(PPh3)2 (30 mg) is mixed in N,N-dimethylformamide (4 mL) and degassed. The solution resulted is heated at 100° C. for 1 hour. After the mixture cooled to room temperature, the N,N-dimethylformamide is removed and the residue is purified through chromatography to afford the title compound (68 mg, 59%). MS (ESI): 444.1 (M+1)+1.

Workup

  1. customdegassed
  2. customThe solution resulted
  3. temperatureAfter the mixture cooled to room temperature
  4. customthe N,N-dimethylformamide is removed
  5. customthe residue is purified through chromatography

Sources & evidence

ORD record
ord-1851b8a07d174a4b99c23d6df282ae3f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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