Allyltributylstannane → HCID 68630168, compound

HRID 1801475Notes

Reaction equation

HRID 1801475 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH2:21]([Sn](CCCC)(CCCC)CCCC)[CH:22]=[CH2:23].[Li+].[Cl-]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:23]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]2)[CH:22]=[CH2:21]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 85911625HCID 85911625, compound

Product 1

HCID 68630168HCID 68630168, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 2-methoxy-quinolin-8-yl ester (3.07 g, 10 mmol, prepared according to WO 2006/021448), allyltributylstannane (3.8 mL, 1.25 eq.), Pd(PPh3)4 (0.29 g, 0.025 eq.) and LiCl (1.6 g, 3.75 eq.) in DMF (20 mL) was stirred at 100° C. for 3 h. After cooling to rt, the mixture was poured on water and extracted with EA. The aq. layer was extracted once more with EA and the combined org. layers were washed with water and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 9:1) to give 8-allyl-2-methoxy-quinoline which was contaminated with stannane residues. This crude oil was dihydroxylated following General Method F using AD-mix β, was affording, after purification by CC (Hept/EA 2:1, 1:1, EA) a colourless solid (2.04 g, 87% yield).

Workup

  1. temperatureAfter cooling to rt
  2. additionthe mixture was poured on water
  3. extractionextracted with EA
  4. extractionThe aq. layer was extracted once more with EA
  5. washlayers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by CC (Hept/EA 9:1)

Sources & evidence

ORD record
ord-7ee4e149acbe43d2bf8f17ab7de78e90
Source dataset
uspto-grants-2013_01
Patent number
US08349828B2

Reaction notes

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