Tributyl(prop-1-yn-1-yl)stannane → HCID 67429823, compound

HRID 1662301Notes

Reaction equation

HRID 1662301 reaction equation
[C@@H:1]1([N:9]2[CH:13]=[C:12](I)[CH:11]=[C:10]2[N+:15]([O-:17])=[O:16])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.[CH2:18]([Sn](CCCC)(CCCC)C#CC)[CH2:19][CH2:20]C>CN(C=O)C.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>[C@@H:1]1([N:9]2[CH:13]=[C:12]([C:18]#[C:19][CH3:20])[CH:11]=[C:10]2[N+:15]([O-:17])=[O:16])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Participants

5

Reactant 2

HCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 67428497HCID 67428497, compound2×

Product 1

HCID 67429823HCID 67429823, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-2-nitropyrrole (Compound 1) (280 mg, 0.79 mmol) and Pd(PPh3)2Cl2 (56 mg, 0.08 mmol) were dissolved in DMF (7.9 ml), followed by addition of tributyl(1-propynyl)tin (481 μl, 1.6 mmol). The reaction mixture was heated at 100° C. for 1.5 hours, concentrated and then purified on a silica gel column (CH2Cl2:MeOH, 50:1, v/v) and by HPLC (34%-35% CH3CN, 13 minutes) to give Compound 2 (125 mg, 60%).

Workup

  1. concentrationconcentrated
  2. custompurified on a silica gel column (CH2Cl2

Sources & evidence

ORD record
ord-4ba97f510ce14b37ad1f81d1ad1f3701
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

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