5-Methoxy-1H-indole-2-carbaldehyde → 2-[(E)-2-(2,6-dichlorophenyl)ethenyl]-5-methoxy-1H-indole

HRID 11067Notes

Reaction equation

HRID 11067 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=O)=[CH:6]2.[Br-].[Cl:15][C:16]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[C:17]=1[CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li+].CC([N-]C(C)C)C>>[Cl:15][C:16]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[C:17]=1/[CH:18]=[CH:12]/[C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2

Participants

4

Reactant 3

HCID 8264565-Methoxy-1H-indole-2-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 118435512,6-Dichlorobenzyltriphenylphosphonium bromide

Product 1

HCID 118431512-[(E)-2-(2,6-dichlorophenyl)ethenyl]-5-methoxy-1H-indole

Procedure

The 5-methoxy-1H-indole-2-carbaldehyde (O) was reacted with (2,6-dichlorobenzyl)(triphenyl)phosphonium bromide (511) prepared as described in example 102 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 1.37:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2/hexane) the diene (512) as a yellow solid (the pure E isomer) (97%), mp 144–147° C. 1H NMR (CDCl3) δ 8.20 (br s, 1H), 7.36 (d, J=8.1 Hz, 1H), 7.27 (m, 1H), 7.25 (d, J=16.8 Hz, 1H), 7.11 (t, J=8.0 Hz, 1H), 7.03 (d, J=2.4 Hz, 1H), 6.93 (d, J=16.8 Hz, 1H), 6.88 (dd, J=8.7, 2.5 Hz, 1H), 6.61 (d, J=1.8 Hz, 1H), 3.86 (s, 3H). Found: C, 64.04; H, 4.13; N, 4.39. C17H13Cl2NO requires C, 64.17; H, 4.12; N, 4.40.

Workup

  1. customprepared
  2. additionadded at 0° C.
  3. customto give
  4. custom(after crystallisation from CH2Cl2/hexane) the diene (512) as a yellow solid (the pure E isomer) (97%), mp 144–147° C

Sources & evidence

ORD record
ord-09c9625c2f0844eb972125fd587329d8
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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