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 1354211노트

반응식

HRID 1354211 반응식
[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

참가 물질

9

반응물 2

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

생성물 1

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

시약·촉매·용매 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3e4cb1a0340c4ed8a97239c3925cc9cb
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223776B2

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