3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde → 3-[2-(N,N-Dimethylamino)ethyl]-5-vinyl-1H-indole

HRID 2427915Notes

Reaction equation

HRID 2427915 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[NH:7][CH:6]=1.[CH3:17]C(C)([O-])C.[K+]>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[CH2:17])[CH:12]=2)[NH:7][CH:6]=1

Participants

5

Reactant 2

HCID 99908943-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 104432413-[2-(N,N-Dimethylamino)ethyl]-5-vinyl-1H-indoleYield 88.7%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde (Example 13) (0.216 g, 1 mmol) in THF (5 mL), methyl triphenyl phosphonium bromide (0.393 g, 1.1 mmol) is added. To the obtained slurry, under an argon atmosphere potassium tert-butoxide (0.118 g, 1.05 mmol) is added in three portions at ambient temperature. When thin layer chromatography (TLC) indicates complete conversion of the aldehyde, the mixture is poured on ice and extracted with ethyl acetate. Removal of the solvent gives a residue which is chromatographed on silica (25 g, CHCl3, MeOH, NEt3 19:1:0.5 v:v:v) to give the title product as pale yellow oil (0.190 g, 88%). 1H-NMR (CDCl3, 300 MHz) δ 2.37 (s, 6H, N(CH3)2); 2.64-2.70 (m, 2H, CH2NMe2); 2.92-2.99 (m, 2H, CH2); 5.13 (d, 1H, J=10.9 Hz, cis H2C═CH); 5.69 (d, 1H, J=17.6 Hz, trans H2C═CH); 6.84 (dd, 1H, H2C═CH); 6.94 (br s, 1H, H-2); 7.24 (d, 1H, J=8.2 Hz, H-7); 7.31 (dd, J=1.8 Hz, H-6); 7.58 (d, 1H, H-4); 8.66 (br s, 1H, NH). 13C-NMR (CDCl3, 75 MHz) δ 24.00 (CH2); 45.73 (N(CH3)2); 60.62 (CH2NMe2); 110.93 (H2C═CH); 111.50 (C-7); 114.66 (C-3); 117.41 (C-4); 120.20 (C-6); 122.42 (C-2); 127.83 (C-5); 129.34 (C-9); 136.45 (C-8); 138.22 (H2C═CH).

Workup

  1. additionthe mixture is poured on ice
  2. extractionextracted with ethyl acetate
  3. customRemoval of the solvent
  4. customgives a residue which
  5. customis chromatographed on silica (25 g, CHCl3, MeOH, NEt3 19:1:0.5 v:v:v)

Sources & evidence

ORD record
ord-191689e5b3ed4726b04bcb5da1478874
Source dataset
uspto-grants-2011_06
Patent number
US07968730B2

Reaction notes

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