Carbon tetrabromide → 7-Chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole

HRID 2174048ノート

反応式

HRID 2174048 の反応式
[Cl:1][C:2]1[C:10]2[N:9]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=2[C:5]([CH:21]=O)=[C:4]([CH3:23])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:43](Br)(Br)([Br:45])[Br:44]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([CH:21]=[C:43]([Br:45])[Br:44])=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 72192144HCID 72192144、化合物

生成物 1

HCID 867016717-Chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 7-chloro-5-methyl-1-tosyl-1H-indole-4-carbaldehyde (48 mg, 0.138 mmol) and PPh3 (109 mg, 0.414 mmol) in DCM (1.4 mL) at 0° C., was added CBr4 (68.6 mg, 0.207 mmol) and the reaction was warmed to room temperature. After 10 minutes the reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.00 (d, J=3.79 Hz, 1H) 7.88 (s, 1H) 7.73 (m, J=8.59 Hz, 2H) 7.42 (m, J=7.83 Hz, 2H) 7.23 (s, 1H) 6.71 (d, J=3.79 Hz, 1H) 2.37 (s, 3H) 2.23 (s, 3H).

後処理

  1. customwas purified by flash chromatography (0-50% EtOAc in heptanes)

出典と根拠

ORDレコード
ord-7d8fac92fc504c1bb117c29e9ba25792
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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