3-Methoxybenzaldehyde → HCID 10111588, 화합물

HRID 428657노트

반응식

HRID 428657 반응식
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)[C:3]#[CH:4].C([Mg]Cl)#C.COC1C=C(C=CC=1)C=O.Br[C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1/[C:30](=[CH:38]/[C:39]1[NH:40][CH:41]=[CH:42][C:43]=1[O:44][CH3:45])/[C:31](=[O:37])[NH:32]2>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.[Cu]I.CN(C=O)C.CCN(CC)CC>[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)[C:3]#[C:4][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1/[C:30](=[CH:38]/[C:39]1[NH:40][CH:41]=[CH:42][C:43]=1[O:44][CH3:45])/[C:31](=[O:37])[NH:32]2

참가 물질

9

반응물 4

HCID 115693-MethoxybenzaldehydeHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2회HCID 183593081-(3-Methoxyphenyl)prop-2-yn-1-olHCID 178462451HCID 178462451, 화합물

생성물 1

HCID 10111588HCID 10111588, 화합물

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Using Method D above, 3-hydroxy-3-(3-methoxyphenyl)-1-propyne (151 mg, 1.0 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to 3-methoxybenzaldehyde (Aldrich) according to Method A above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (Starting Material 1) (220 mg, 0.69 mmol) using (Ph3P)2PdCl2 (100 mg) (Aldrich) and CuI (55 mg) (Aldrich) as catalyst in DMF (5 mL) and Et3N (5 mL) as solvent at 70° C. for 18 h, yielding rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(3-methoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 66 mg, 24%).

출처 및 근거

ORD 기록
ord-5e2b5f8ae2db4bf98b4d0d50b8325be3
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313310B1

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