Lithium diisopropylamide → HCID 11843963, compound

HRID 11074Notes

Reaction equation

HRID 11074 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]=[CH:45][C:24]=1[CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li+].[CH3:50]C([N-]C(C)C)C>>[Br:22][C:23]1[CH:48]=[CH:47][CH:46]=[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][CH3:50])=[CH:14][CH:13]=2

Participants

4

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 11733967Phosphonium, [(2-bromophenyl)methyl]triphenyl-, bromideHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 11843963HCID 11843963, compound

Procedure

The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-bromobenzyl)(triphenyl)phosphonium bromide using the procedure described in example 37, except that the aldehyde was added at 0° C., the ratio of LDA:aldehyde was 1.46:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2/hexane) the diene (531) as a yellow solid (the pure E isomer) (88%), mp 120–123° C. 1H NMR (CDCl3) δ 8.21 (br s, 1H), 7.66 (dd, J=7.9, 1.5 Hz, 1H), 7.59 (dd, J=8.1, 1.0 Hz, 1H), 7.32 (br t, J=7.1 Hz, 1H), 7.27 (d, J=8.3 Hz, 1H), 7.22 (d, J=16.4 Hz, 1H), 7.12 (td, J=7.6, 1.5 Hz, 1H), 7.05 (d, J=16.4 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.88 (dd, J=8.8, 2.4 Hz, 1H), 6.59 (d, J=1.7 Hz, 1H), 3.86 (s, 3H). Found: C, 61.97; H, 4.30; N, 4.17. C17H14BrNO requires C, 62.21; H, 4.30; N, 4.27.

Workup

  1. additionwas added at 0° C.
  2. customto give
  3. custom(after crystallisation from CH2Cl2/hexane) the diene (531) as a yellow solid (the pure E isomer) (88%), mp 120–123° C

Sources & evidence

ORD record
ord-1db8bc6974f04497a060aa2801e1f53f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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