Allyltributylstannane → 8-Allyl-7-chloro-2-methoxy-[1,5]naphthyridine

HRID 1259841Notes

Reaction equation

HRID 1259841 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1OS(C(F)(F)F)(=O)=O)=[N:9][C:8]([O:20][CH3:21])=[CH:7][CH:6]=2.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>CN(C=O)C>[CH2:24]([C:11]1[C:2]([Cl:1])=[CH:3][N:4]=[C:5]2[C:10]=1[N:9]=[C:8]([O:20][CH3:21])[CH:7]=[CH:6]2)[CH:23]=[CH2:22]

Participants

4

Reactant 2

HCID 90628AllyltributylstannaneHCID 86613542Trifluoromethanesulfonic acid 3-chloro-6-methoxy-[1,5]naphthyridin-4-yl ester

Product 1

HCID 671828908-Allyl-7-chloro-2-methoxy-[1,5]naphthyridineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A flask charged with trifluoromethanesulfonic acid 3-chloro-6-methoxy-[1,5]naphthyridin-4-yl ester (1.50 g; prepared according to WO 2004/058144), allyltributylstannane (1.68 g) and DMF was degassed with N2. The reaction mixture was treated with LiCl (695 mg) and Pd(PPh3)4 (126 mg) and further stirred at 100° C. for 4 h. After cooling, the mixture was poured into 10% aq. NH4OH and EA, the aq. layer was extracted with EA and the combined org. layers were washed with water (2×) and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 4:1), affording a yellow oil (795 mg; 77% yield).

Workup

  1. customwas degassed with N2
  2. additionThe reaction mixture was treated with LiCl (695 mg) and Pd(PPh3)4 (126 mg)
  3. temperatureAfter cooling
  4. additionthe mixture was poured into 10% aq. NH4OH and EA
  5. extractionthe aq. layer was extracted with EA
  6. washlayers were washed with water (2×) and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by CC (Hept/EA 4:1)
  10. customaffording a yellow oil (795 mg; 77% yield)

Sources & evidence

ORD record
ord-218db01b57434a92bcc8829141098790
Source dataset
uspto-grants-2013_06
Patent number
US08466168B2

Reaction notes

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