Lithium diisopropylamide → 2-[(E)-2-(2-chloro-5-methoxyphenyl)ethenyl]-5-methoxy-1H-indole

HRID 11087

반응식

HRID 11087 반응식
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=C(I)C4C(=O)NC(=O)C=4[C:5]=3[C:4]=2[CH:3]=1.[Br-].[Cl:22][C:23]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][C:24]=1[CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li+].[CH3:52]C([N-]C(C)C)C>>[Cl:22][C:23]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][C:24]=1/[CH:25]=[CH:9]/[C:10]1[NH:11][C:12]2[C:4]([CH:5]=1)=[CH:3][C:2]([O:1][CH3:52])=[CH:14][CH:13]=2

참가 물질

4

반응물 3

HCID 2724682Lithium diisopropylamide2회HCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 85758264(2-Chloro-5-methoxybenzyl)(triphenyl)phosphonium bromide

생성물 1

HCID 118442202-[(E)-2-(2-chloro-5-methoxyphenyl)ethenyl]-5-methoxy-1H-indole

실험 절차

The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-chloro-5-methoxybenzyl)(triphenyl)phosphonium bromide (578) prepared as described in example 166 using the procedure described in example 37, except that the LDA and aldehyde were (sequentially) added at 0° C., the ratio of LDA:aldehyde was 1.5:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2/hexane) the diene (579) as a pale yellow solid (the pure E isomer) (85%), mp 119–121° C. 1H NMR (CDCl3) δ 8.22 (br s, 1H), 7.29 (d, J=8.9 Hz, 1H), 7.26 (br d, J=8.7 Hz, 1H), 7.22 (d, J=16.5 Hz, 1H), 7.18 (d, J=3.0 Hz, 1H), 7.06 (d, J=16.7 Hz, 1H), 7.04 (br s, 1H), 6.88 (dd, J=8.7, 2.5 Hz, 1H), 6.77 (dd, J=8.8, 3.0 Hz, 1H), 6.59 (d, J=1.8 Hz, 1H), 3.86 (s, 3H), 3.85 (s, 3H). Found: C, 68.70; H, 5.11; N, 4.37. C18H16ClNO2 requires C, 68.90; H, 5.14; N, 4.46.

후처리

  1. customprepared
  2. additionadded at 0° C.
  3. customto give
  4. custom(after crystallisation from CH2Cl2/hexane) the diene (579) as a pale yellow solid (the pure E isomer) (85%), mp 119–121° C

출처 및 근거

ORD 기록
ord-75df05aa2dc442c2a14c9e3dbed3c708
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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