Lithium diisopropylamide → 5-(Benzyloxy)-2-[(e)-2-(2-methoxy-4-nitrophenyl)ethenyl]-1h-indole

HRID 11149Notes

Reaction equation

HRID 11149 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH:18]=O)=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[CH3:21][O:22][C:23]1[CH:48]=[C:47]([N+:49]([O-:51])=[O:50])[CH:46]=[CH:45][C:24]=1[CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li+].CC([N-]C(C)C)C>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](/[CH:18]=[CH:25]/[C:24]1[CH:45]=[CH:46][C:47]([N+:49]([O-:51])=[O:50])=[CH:48][C:23]=1[O:22][CH3:21])=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamide2×HCID 10562696HCID 10562696, compoundHCID 87898968(2-Methoxy-4-nitrobenzyl)(triphenyl)phosphonium bromide

Product 1

HCID 219807495-(Benzyloxy)-2-[(e)-2-(2-methoxy-4-nitrophenyl)ethenyl]-1h-indole

Procedure

The aldehyde (846) was reacted with (2-methoxy-4-nitrobenzyl) (triphenyl)phosphonium bromide (582) prepared as described in example 432 using the procedure described in method 2, 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/pentane) the diene (583) as an orange solid (the pure E isomer) (63%), mp 156–159° C. 1H NMR (CDCl3) δ 8.23 (br s, 1H), 7.87 (dd, J=8.5, 2.1 Hz, 1H), 7.76 (d, J=2.2 Hz, 1H), 7.68 (d, J=8.6 Hz, 1H), 7.48 (d, J=7.3 Hz, 2H), 7.39 (t, J=7.3 Hz, 2H), 7.32 (t, J=7.2 Hz, 1H), 7.28 (d, J=17.1 Hz, 1H), 7.26 (d, J=8.7 Hz, 1H), 7.20 (d, J=16.7 Hz, 1H), 7.12 (d, J=2.4 Hz, 1H), 6.97 (dd, J=8.7, 2.5 Hz, 1H), 6.63 (br s, 1H), 5.11 (s, 2H), 4.01 (s, 3H). Found: C, 71.69; H, 4.94; N, 7.11. C24H20N2O4 requires C, 71.99; H, 5.03; N, 7.00.

Workup

  1. customprepared
  2. additionadded at 0° C.
  3. customto give
  4. custom(after crystallisation from CH2Cl2/pentane) the diene (583) as an orange solid (the pure E isomer) (63%), mp 156–159° C

Sources & evidence

ORD record
ord-a8cb584bc0fb4a4fa0534eb7424f8082
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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