Tetrahydrofuran → HCID 90302550, compound

HRID 531429Notes

Reaction equation

HRID 531429 reaction equation
C1(NC(C2C(C(OCCCCCC)=O)=CSC=2)=O)C=CC=CC=1.[Br:24][C:25]1[S:26][C:27]([Br:48])=[C:28]([C:39](=[O:47])[NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:29]=1[C:30]([O:32]CCCCCC)=[O:31].C([O-])([O-])=O.[Cs+].[Cs+].O1CCCC1>[Pd].CO>[Br:24][C:25]1[S:26][C:27]([Br:48])=[C:28]([C:39](=[O:47])[NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:29]=1[C:30]([OH:32])=[O:31]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 90302644HCID 90302644, compoundHCID 90302656HCID 90302656, compound

Product 1

HCID 90302550HCID 90302550, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hexyl 4-(phenylcarbamoyl)thiophene-3-carboxylate (4) (0.2949 g, 0.000890 mol), hexyl 2,5-dibromo-4-(phenylcarbamoyl)thiophene-3-carboxylate (7) (0.2952 g, 0.000890 mol), palladium catalyst (4% mol), ligand (8% mol) and Cs2CO3 (162.9 mg; 0.50 mmol) were put in a microwave vial with a magnetic stirring bar. Tetrahydrofuran (1 mL) was added and sealed. 5 cycles of freeze pump thaw was done and the reaction was kept at 120 degree Celsius for 48 hours. The whole mixture was cooled to room temperature and poured in 500 mL of cold methanol. The precipitate was filtered and dissolved in THF and precipitated again. This procedure was repeated 3 times to remove small molecules.

Workup

  1. customsealed
  2. filtrationThe precipitate was filtered
  3. dissolutiondissolved in THF
  4. customprecipitated again
  5. customto remove small molecules

Sources & evidence

ORD record
ord-5195d90d83394261b46cf2954f2730da
Source dataset
uspto-grants-2016_05
Patent number
US09355787B2

Reaction notes

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