Sodium Carbonate → Biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)-[4-(8,8-diphenyl-8H-indolo[3,2,1-de]acridin-3-yl)phenyl]amine

HRID 2277361ノート

反応式

HRID 2277361 の反応式
[C:1]1([C:7]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:20]3[C:15]4=[C:16]([C:21]5[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=5[N:14]4[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=4)[CH:17]=[CH:18][CH:19]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36]1([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH:41]=[CH:40][C:39]([N:42]([C:58]2[CH:63]=[CH:62][C:61](Br)=[CH:60][CH:59]=2)[C:43]2[CH:55]=[CH:54][C:53]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:46]([CH3:57])([CH3:56])[C:45]=3[CH:44]=2)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:36]1([C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH:37]=[CH:38][C:39]([N:42]([C:43]2[CH:55]=[CH:54][C:53]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:46]([CH3:57])([CH3:56])[C:45]=3[CH:44]=2)[C:58]2[CH:63]=[CH:62][C:61]([C:23]3[CH:24]=[CH:25][C:26]4[N:14]5[C:13]6[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=6[C:7]([C:30]6[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=6)([C:1]6[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=6)[C:20]6[C:15]5=[C:16]([CH:17]=[CH:18][CH:19]=6)[C:21]=4[CH:22]=3)=[CH:60][CH:59]=2)=[CH:40][CH:41]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 58131689N-((1,1'-Biphenyl)-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amineHCID 681691638,8-diphenyl-8H-indolo[3,2,1-de]acridine-3-boronic acid

生成物 1

HCID 67324655Biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)-[4-(8,8-diphenyl-8H-indolo[3,2,1-de]acridin-3-yl)phenyl]amine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

85 g (190 mmol) of 8,8-diphenyl-8H-indolo[3,2,1-de]acridine-3-boronic acid, 98 g (190 mmol) of biphenyl-4-yl-(4-bromophenyl)-(9,9-dimethyl-9H-fluoren-2-yl)amine and 13 g (123 mmol) of sodium carbonate are suspended in 180 ml of toluene, 180 ml of dioxane and 60 ml of water. 3.0 mg mmol) of Pd(PPh3)4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum. The purity is 99.9%. The yield is 124 g (147 mmol), corresponding to 78% of theory.

後処理

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

出典と根拠

ORDレコード
ord-00d8f3eaf326453eb5cfab3a287d2a2b
出典データセット
uspto-grants-2015_09
特許番号
US09133119B2

反応ノート

読み込み中…