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

HRID 11075Notes

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.[Cl-].[N+:22]([C:25]1[CH:50]=[CH:49][CH:48]=[CH:47][C:26]=1[CH2:27][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O-:24])=[O:23].[Li+].[CH3:52]C([N-]C(C)C)C>>[CH3:52][O:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](/[CH:9]=[CH:27]/[C:26]1[CH:47]=[CH:48][CH:49]=[CH:50][C:25]=1[N+:22]([O-:24])=[O:23])=[CH:5]2

Participants

Reactant 3

HCID 2724682Lithium diisopropylamide

HCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HCID 22174467HCID 22174467, compound

Product 1

HCID 118435545-methoxy-2-[(E)-2-(2-nitrophenyl)ethenyl]-1H-indole

Procedure

The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-nitrobenzyl)(triphenyl)phosphonium chloride 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 (536) as red-orange crystals (the pure E isomer) (47%), mp 136–138° C. 1H NMR (CDCl3) δ 8.25 (br s, 1H), 7.98 (dd, J=8.2, 1.2 Hz, 1H), 7.78 (dd, J=7.9, 1.0 Hz, 1H), 7.61 (td, J=7.6, 0.9 Hz, 1H), 7.41 (d, J=16.3 Hz, 1H), 7.39 (td, J=7.8, 1.3 Hz, 1H), 7.27 (m, 1H), 7.13 (d, J=16.3 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.90 (dd, J=8.8, 2.5 Hz, 1H), 6.62 (d, J=1.8 Hz, 1H), 3.86 (s, 3H). Found: C, 69.44; H, 4.49; N, 9.70. C17H14N2O3 requires C, 69.38; H, 4.79; N, 9.52.

Workup

customto give
custom(after crystallisation from CH2Cl2/hexane) the diene (536) as red-orange crystals (the pure E isomer) (47%), mp 136–138° C

Sources & evidence

ORD record: ord-9657ba143e4645cb9448f995c724a097
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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