Dichloromethane → HCID 18931465、化合物

HRID 1598968

反応式

HRID 1598968 の反応式
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:4][CH2:3]1.[F:22][C:23]1[CH:33]=[C:32](I)[CH:31]=[CH:30][C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(CC)CC)C.C(Cl)Cl>[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.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:32]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([F:22])[CH:33]=3)=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH2:4][CH2:3]1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 18761561Ethyl 2-fluoro-4-iodobenzoateHCID 18931462HCID 18931462、化合物2 回

生成物 1

HCID 18931465HCID 18931465、化合物

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 0.20 g (0.72 mmol) of 4,4-dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)-7-ethynylquinoline (Compound 3) and 0.39 g (1.5 mmol) of ethyl 2-fluoro-4-iodobenzoate were added 2.9 g (4.0 mL, 29 mmol) of triethylamine, 0.029 g (0.15 mmol) of copper(I) iodide, and 0.113 g (0.16 mmol) of bis(triphenylphosphine)palladium(II) chloride, consecutively. The resulting mixture was stirred at room temperature for 20 hours. Methylene chloride was added and the reaction was adsorbed onto silica gel. The product was obtained by flash chromatography (5% ethyl acetate in hexanes) followed by recrystallization in ethanol to give the title compound as orange crystals. PNMR (300 MHz, CDCl3) d 1.37 (6 H, s), 1.40 (3 H, t, J=7.1 Hz), 1.86 (2 H, t, J=6.0 Hz), 2.38 (3 H, s), 3.61 (2 H, t, J=6.0 Hz), 4.39 (2 H, q, J=7.1 Hz), 6.77 (1 H, d, J=1.7 Hz), 6.87 (1 H, dd, J=7.9, 1.7 Hz), 7.23-7.28 (7 H, m), 7.86 (1 H, t, J=7.8 Hz).

後処理

  1. customfollowed by recrystallization in ethanol

出典と根拠

ORDレコード
ord-f2e3a1033424478480f53a185bcf10f2
出典データセット
uspto-grants-1998_04
特許番号
US05739338

関連ノート

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