Dichloromethane → HCID 18931465, 화합물

HRID 1598968

반응식

HRID 1598968 반응식
[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

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 18761561Ethyl 2-fluoro-4-iodobenzoateHCID 18931462HCID 18931462, 화합물2회

생성물 1

HCID 18931465HCID 18931465, 화합물

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  1. customfollowed by recrystallization in ethanol

출처 및 근거

ORD 기록
ord-f2e3a1033424478480f53a185bcf10f2
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739338

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