Sodium Carbonate → HCID 10296814, compound

HRID 651752Notes

Reaction equation

HRID 651752 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[C:13](=[O:28])[NH:14][C:15](=[O:27])[C:16]=3[C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH3:26])[CH:18]=3)=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[S:29]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([C:16]2[C:15](=[O:27])[NH:14][C:13](=[O:28])[C:12]=2[C:6]2[C:5]3[C:9](=[CH:10][C:2]([C:31]4[CH:32]=[CH:33][S:29][CH:30]=4)=[CH:3][CH:4]=3)[N:8]([CH3:11])[CH:7]=2)=[CH:18]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 21709059HCID 21709059, compound

Product 1

HCID 10296814HCID 10296814, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

Argon was bubbled through a solution of 3-(6-bromo-1-methyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione (160 mg, 0.37 mmol) in dioxane (15 mL) for 10 min. Tetrakis(triphenylphosphine)palladium (0) (8.5 mg, 0.007 mmol) and thiophene-3-boronic acid (52 mg, 0.41 mmol) and aqueous Na2CO3 (0.37 mL, 2M) were added. The mixture was refluxed for 2 h and more tetrakis(triphenylphosphine)palladium (0) (20 mg, 0.01 mmol) was added. Refluxing was continued for 24 h. The mixture was cooled and evaporated. Chromatography of the residue over silica using 50% EtOAc in hexane gave 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-thiophen-3-yl-1H-indol-3-yl)pyrrole-2,5-dione (117 mg, 72%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperatureRefluxing
  3. temperatureThe mixture was cooled
  4. customevaporated

Sources & evidence

ORD record
ord-e7c95a9010ff4701858d309e3b9d0e48
Source dataset
uspto-grants-2001_08
Patent number
US06281356B1

Reaction notes

Loading…