Toluene → 5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde

HRID 221171ノート

反応式

HRID 221171 の反応式
Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.[CH:24]([C:26]1[S:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[CH2:16]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[C:9]1[CH:10]=[C:11]2[C:6]([C:5]3[CH:4]=[CH:3][C:2]([C:29]4[S:30][C:26]([CH:24]=[O:25])=[CH:27][CH:28]=4)=[CH:14][C:13]=3[CH2:12]2)=[CH:7][CH:8]=1)[CH2:17][CH2:18][CH3:19]

参加物

7

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27734305-Formyl-2-thiopheneboronic acidHCID 59325934(7-bromo-9H-fluoren-2-yl)-dibutyl amine

生成物 1

HCID 866417785-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

Under N2 atmosphere, 0.37 parts of (7-bromo-9H-fluoren-2-yl)-dibutyl amine (11), 0.19 parts of 5-formyl-2-thiopheneboronic acid, 0.41 parts of potassium carbonate, and 0.16 parts of PdCl2(dppf) were added into 5 parts of toluene and 5 parts of CH3OH, followed by stirring and mixing. Then, the reaction mixture was heated to 60° C. and reacted for 18 hours. After the reaction mixture was quenched by water, using the diethyl ether to extract the product, and magnesium sulfate was used for dehydration. After removing the solvent, the residual was purified with chromatography method column by using dichloromethane/hexane co-solvent as an eluent, to obtain a compound (12a) of the present example. This compound was in a form of a tangerine solid, and the yield of this compound was 61%.

後処理

  1. additionmixing
  2. customreacted for 18 hours
  3. customAfter the reaction mixture was quenched by water
  4. extractionto extract the product, and magnesium sulfate
  5. customAfter removing the solvent
  6. customthe residual was purified with chromatography method column

出典と根拠

ORDレコード
ord-3e2a5e86bdab425d91eabff798068d49
出典データセット
uspto-grants-2012_06
特許番号
US08203068B2

反応ノート

読み込み中…