Hexane → [2-(2,4-Dimethoxyphenyl)-6-methoxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 609821노트

반응식

HRID 609821 반응식
CN(C)[C:3]1[S:4][C:5]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=2[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:11]=1)=[O:9].[CH3:32][O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[Mg]Br.CCCCCC.C(OCC)(=O)C>C1COCC1.CO>[CH3:32][O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[C:3]1[S:4][C:5]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=2[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:11]=1)=[O:9]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178491918HCID 178491918, 화합물

생성물 1

HCID 10554255[2-(2,4-Dimethoxyphenyl)-6-methoxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone수율 58.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (2.0 g, 4.6 mmol) in THF (17 mL) was treated with a 1.8 M THF solution of 2,4-dimethoxyphenylmagnesium bromide (12.5 mL, 22.5 mmol) (prepared from 2,4-dimethoxybromobenzene, catalytic iodine, and magnesium turnings) to provide, after chromatography (silica gel, 1:1 hexane:ethyl acetate, 0-10% MeOH) 1.43 g (58%) of the title compound as a pale green, fluffy solid: 1H NMR d 1.44 (m, 2H), 1.60 (m, 4H), 2.49 (m, 4H), 2.74 (t, J=6.0 Hz, 2H), 3.49 (s, 3H), 3.75 (s, 3H), 3.87 (s, 3H), 4.07 (t, J=6.0 Hz, 2H), 6.21 (d, J=2.2 Hz, 1H), 6.42 (dd, J=2.3, 8.5 Hz, 1H), 6.74 (d, J=8.8 Hz, 2H), 6.95 (dd, J=2.3, 8.9 Hz, 1H), 7.30-7.33 (m, 2H), 7.63 (d, J=8.9 Hz, 1H), 7.74 (d, J=8.7 Hz, 2H); 13C NMR d 24.2, 26.0, 54.7, 55.2, 55.5, 55.7, 57.9, 66.3, 98.6, 104.4, 104.8, 113.8, 114.7, 115.7, 124.6, 130.7, 131.4, 132.0, 132.2, 133.7, 140.1, 140.4, 157.1, 157.5, 161.5, 162.5, 192.0; IR (CHCl3) 1644, 1601 cm-1 ; MS (FD) m/e 531 (M+); Anal. calc'd. for C31H33NO5S: C, 70.03; H, 6.26; N, 2.63. Found: C, 70.24; H, 6.35; N, 2.66.

후처리

  1. customto provide

출처 및 근거

ORD 기록
ord-11cd0892def34e95a4154cc81988dad2
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998442

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