Sodium Carbonate → HCID 70267344、化合物

HRID 1871165ノート

反応式

HRID 1871165 の反応式
[C:1]1([N:7]([C:14]2[CH:26]=[CH:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:16]=3[C:15]=2Br)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C(O)C>[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[C:1]1[CH:6]=[CH:5][C:4]([C:20]2[CH:19]=[C:18]3[C:23]([C:24]4[CH:25]=[CH:26][C:14]([N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)=[CH:15][C:16]=4[C:17]3([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:22][CH:21]=2)=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 18694822HCID 18694822、化合物HCID 223525161,3-Benzothiazol-2-ylboronic acid

生成物 1

HCID 70267344HCID 70267344、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
87.5 °C

実験手順

A mixture of diphenylamino-9,9-diethyl-bromofluorene (7.02g, 0.015 mol), benzothiazole boronic acid (7.5 g 0.029 mol.), ethanol (50 ml), in NMP (50 ml) was degassed by bubbling nitrogen through the solution for 20 min. Sodium carbonate (13.0 g, 0.12 mol.) and 5% palladium on charcoal (1.5 g ) were then added, the mixture heated at 85-90° C. for 42 hrs. The resulting solids (18.0 g) that separated upon cooling were collected, washed with ethanol and dried. The solids were then transferred to a chromatograph column containing 300 g of alumina. Elution with 1:1 toluene-heptane gave the product, 4.98 g. (55.5% yield), m.p. 243.6-246.1° C. Recrystallization from toluene did not raise the melting point. Mass Spec: m/z 598, (M+). Analysis calculated for C42H34N2S: C, 84.25; H, 5.72; N, 4.68; S, 5.34. Found: C, 83.87; H, 6.02; N, 5.04; S, 5.29.

後処理

  1. customin NMP (50 ml) was degassed
  2. customby bubbling nitrogen through the solution for 20 min
  3. customThe resulting solids (18.0 g) that separated
  4. temperatureupon cooling
  5. customwere collected
  6. washwashed with ethanol
  7. customdried
  8. additioncontaining 300 g of alumina
  9. washElution with 1:1 toluene-heptane
  10. customgave the product, 4.98 g
  11. customRecrystallization from toluene
  12. temperaturedid not raise the melting point

出典と根拠

ORDレコード
ord-fe6d77122f2847db9daddfcc8daa2df4
出典データセット
uspto-grants-2000_08
特許番号
US06100405

反応ノート

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