8-Ethynyl-1,4-dioxaspiro[4.5]decan-8-ol → 8-(6-Methoxy-[1,5]naphthyridin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1354211Notes

Reaction equation

HRID 1354211 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2OS(C(F)(F)F)(=O)=O.[C:21]([C:23]1([OH:33])[CH2:32][CH2:31][C:26]2([O:30][CH2:29][CH2:28][O:27]2)[CH2:25][CH2:24]1)#[CH:22]>CN(C=O)C.C(N(CC)CC)C.O.CCOCC.[Cu]I.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>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:22]#[C:21][C:23]1([OH:33])[CH2:32][CH2:31][C:26]2([O:27][CH2:28][CH2:29][O:30]2)[CH2:25][CH2:24]1

Participants

9

Reactant 2

HCID 111059858-Ethynyl-1,4-dioxaspiro[4.5]decan-8-olHCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

Product 1

HCID 211046678-(6-Methoxy-[1,5]naphthyridin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol

Reagents, catalysts & solvents 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

A degassed solution of trifluoromethanesulphonic acid 6-methoxy-[1,5]naphthyridin-4-yl ester (986 mg, 3.2 mmol) (WO 03 010138) and 8-ethynyl-1,4-dioxa-spiro[4.5]decan-8-ol (638 mg, 3.5 mmol) (prepared according to J. Chem. Soc. Perk. Trans. 1, 2000, 3382) in DMF (3 ml) was added dropwise to a likewise degassed suspension of copper(I) iodide (50 mg) and PdCl2(PPh3)2 (100 mg) in DMF (2 ml) and triethylamine (3 ml). The reaction mixture was stirred at room temperature for 30 minutes and diluted with water and ether, and the organic phase was washed with water, saturated ammonium chloride solution and saturated sodium chloride solution, dried over MgSO4 and concentrated. The crude product was purified by chromatography on silica gel (hex/EtOAc 1:1, EtOAc).

Workup

  1. washthe organic phase was washed with water, saturated ammonium chloride solution and saturated sodium chloride solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography on silica gel (hex/EtOAc 1:1, EtOAc)

Sources & evidence

ORD record
ord-3e4cb1a0340c4ed8a97239c3925cc9cb
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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