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

HRID 71039ノート

反応式

HRID 71039 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fc1974ae3ec64dd49a5ce6553fb3cee2
出典データセット
uspto-grants-2014_09
特許番号
US08822702B2

反応ノート

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