Lithium diisopropylamide → 2-[(E)-2-(2,6-dibromophenyl)ethenyl]-5-methoxy-1H-indole

HRID 11069Notes

Reaction equation

HRID 11069 reaction equation
[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-].[Br:22][C:23]1[CH:48]=[CH:47][CH:46]=[C:45]([Br:49])[C:24]=1[CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li+].[CH3:51]C([N-]C(C)C)C>>[Br:49][C:45]1[CH:46]=[CH:47][CH:48]=[C:23]([Br:22])[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][CH3:51])=[CH:14][CH:13]=2

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 87899089(2,6-Dibromobenzyl)(triphenyl)phosphonium bromide

Product 1

HCID 219805242-[(E)-2-(2,6-dibromophenyl)ethenyl]-5-methoxy-1H-indole

Procedure

The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2,6-dibromobenzyl)(triphenyl)phosphonium bromide (516) prepared as described in example 107 using the procedure described in example 37, except that the ratio of LDA:aldehyde was 1.37:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2/hexane) the diene (517) as a yellow solid (the pure E isomer) (80%), mp 140–141° C. 1H NMR (CDCl3) δ 8.20 (br s, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.27 (d, J=8.2 Hz, 1H), 7.05 (br s, 1H), 7.03 (d, J=16.7 Hz, 1H), 6.96 (t, J=8.0 Hz, 1H), 6.88 (dd, J=8.7, 2.5 Hz, 1H), 6.82 (d, J=16.7 Hz, 1H), 6.61 (d, J=1.9 Hz, 1H), 3.86 (s, 3H). Found: C, 50.37; H, 3.24; N, 3.37. C17H13Br2NO requires C, 50.16; H, 3.22; N, 3.44.

Workup

  1. customprepared
  2. customto give
  3. custom(after crystallisation from CH2Cl2/hexane) the diene (517) as a yellow solid (the pure E isomer) (80%), mp 140–141° C

Sources & evidence

ORD record
ord-59650bb3fb5849e1898bd638217fd9f7
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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