2-(Tri-n-butylstannyl)thiophene → HCID 71268199, compound

HRID 926431Notes

Reaction equation

HRID 926431 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.[C@@H:19]1([N:27]2[CH:31]=[C:30](I)[CH:29]=[C:28]2[N+:33]([O-:35])=[O:34])[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[CH2:20]1>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.CN(C=O)C>[C@@H:19]1([N:27]2[CH:31]=[C:30]([C:6]3[S:7][CH:8]=[CH:9][CH:10]=3)[CH:29]=[C:28]2[N+:33]([O-:35])=[O:34])[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[CH2:20]1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 67428497HCID 67428497, compound

Product 1

HCID 71268199HCID 71268199, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(Tributylstannyl)thiophene (476 μL, 1.5 mmol) was added to a DMF (2.5 mL) solution containing 1-(2-deoxy-β-D-ribofuranosyl)-4-iodo-2-nitropyrrole (177 mg, 0.5 mmol) and bis(triphenylphosphine)palladium(II) dichloride (18 mg, 0.025 mmol). The mixture was reacted at 100° C. for 30 minutes in a microwave machine (standard mode). The reaction solution was separated between ethyl acetate (50 mL) and water (50 mL). The organic layer was concentrated and purified by HPLC to yield 1-(2-deoxy-β-D-ribofuranosyl)-4-(thien-2-yl)-2-nitropyrrole (97 mg, 0.32 mmol, 63%).

Workup

  1. customThe mixture was reacted at 100° C. for 30 minutes in a microwave machine (standard mode)
  2. customThe reaction solution was separated between ethyl acetate (50 mL) and water (50 mL)
  3. concentrationThe organic layer was concentrated
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-6ba9b98c7dec42908d326081d6b00494
Source dataset
uspto-grants-2016_03
Patent number
US09285319B2

Reaction notes

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