Dimethylformamide → HCID 58434902, compound

HRID 1909827Notes

Reaction equation

HRID 1909827 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:10](=O)[NH:9][C:8]2=[C:12]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13](=[O:15])[NH:14][C:7]=12.[C:21]([O-:24])([O-])=O.[Cs+].[Cs+].CN(C=O)C.[CH2:32]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37]I)[CH2:33][CH2:34][CH3:35]>CCCCCC>[CH2:32]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][N:14]1[C:13](=[O:15])[C:12]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[C:8]2[N:9]([CH2:10][CH:6]([CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8][CH2:12][CH2:16][CH2:20][CH3:19])[C:21](=[O:24])[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[C:7]12)[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 58434872HCID 58434872, compoundHCID 178516981HCID 178516981, compound

Product 1

HCID 58434902HCID 58434902, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a round bottom flask under nitrogen, 3,6-di-thiophen-2-yl-1,4-dihydropyrrolo[3,2-b]pyrrole-2,5-dione (Example 2A, 1.8 g, 6 mmol), Cs2CO3 (4.89 g, mmol) and anhydrous DMF (60 mL) were added and stirred at 60° C. 2-Butyloctyl iodide (3.0 mL, 12 mmol) was added in one portion and the reaction mixture was kept at 60° C. for 24 hours. After removing the solvent, chloroform (30 mL) was added and the mixture was stirred for 10 minutes before it was filtered through coarse Celite® diatomaceous earth particles. After concentration, the crude was purified by a short column with a 3:1 mixture of chloroform:hexane as the eluent to give an orange solid (500 mg, yield 13%). 1H NMR (CDCl3, 500 MHz), δ=7.62 (d, J=5.0 Hz, 2H), 7.30 (d, J=3.5 Hz, 2H), 7.13 (dd, J=5.0, 3.5 Hz, 2H), 3.74 (d, J=7.5 Hz, 4H), 1.40-1.00 (m, 38H), 0.87 (t, J=7.5 Hz, 6H), 0.83 (t, J=7.0 Hz, 6H).

Workup

  1. customAfter removing the solvent, chloroform (30 mL)
  2. additionwas added
  3. stirringthe mixture was stirred for 10 minutes before it
  4. filtrationwas filtered through coarse Celite® diatomaceous earth particles
  5. concentrationAfter concentration
  6. customthe crude was purified by a short column with a 3:1 mixture of chloroform

Sources & evidence

ORD record
ord-fa20d219b2af4f1993df2e1bbdf2a89e
Source dataset
uspto-grants-2013_12
Patent number
US08598448B2

Reaction notes

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