Toluene → HCID 57967304、化合物

HRID 535244ノート

反応式

HRID 535244 の反応式
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[O:23][C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:31]1([C:41]2[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=2)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].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(O)C>[C:31]1([C:41]2[CH:46]=[CH:45][C:44]([C:2]3[C:3]4[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=4)[C:9]([C:16]4[CH:17]=[CH:18][C:19]([C:22]5[O:23][C:24]6[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=6[N:26]=5)=[CH:20][CH:21]=4)=[C:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:43][CH:42]=2)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 441193994-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)HCID 57967305HCID 57967305、化合物

生成物 1

HCID 57967304HCID 57967304、化合物収率 95.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

In a 50 mL three-neck flask, 0.97 g (2.2 mmol) of 2-[4-(10-bromo-9-anthryl)phenyl]benzoxazole, 0.57 g (2.3 mmol) of 4-(1-naphthyl)phenylboronic acid, 0.46 g (4.3 mmol) of sodium carbonate, 15 mL of toluene, 3 mL of ethanol, and 3 mL of water were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 35 mg (0.030 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 100° C. for 18 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the obtained filtrate was condensed to give a solid. The solid was purified by silica gel column chromatograghy (toluene:hexane=2:1) and recrystallized with toluene/hexane, giving 1.2 g of the target white powder in a yield of 94%.

後処理

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 100° C. for 18 hours
  3. waitAfter a certain period
  4. extractionan aqueous layer was extracted with toluene
  5. extractionThe obtained extracted solution
  6. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline
  7. dry with materialthe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. customcondensed
  10. customto give a solid
  11. customThe solid was purified by silica gel column chromatograghy (toluene:hexane=2:1)
  12. customrecrystallized with toluene/hexane

出典と根拠

ORDレコード
ord-2286aba909da4fcf85f4c8e4c391ee6b
出典データセット
uspto-grants-2014_10
特許番号
US08859108B2

反応ノート

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