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 1354211ノート

反応式

HRID 1354211 の反応式
[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

参加物

9

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3e4cb1a0340c4ed8a97239c3925cc9cb
出典データセット
uspto-grants-2007_05
特許番号
US07223776B2

反応ノート

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