Toluene → 4-[5-(1,1-Dioxidothiomorpholin-4-yl)-3-nitropyridin-2-yl]morpholine

HRID 1431261ノート

反応式

HRID 1431261 の反応式
Cl[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH:17]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[CH2:19][CH2:18]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:23]=[S:20]1(=[O:24])[CH2:21][CH2:22][N:17]([C:2]2[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[N:6][CH:7]=2)[CH2:18][CH2:19]1

参加物

7

反応物 5

HCID 1140TolueneHCID 6484228Thiomorpholine 1,1-dioxideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 596312064-(5-Chloro-3-nitropyridin-2-yl)morpholine

生成物 1

HCID 596313874-[5-(1,1-Dioxidothiomorpholin-4-yl)-3-nitropyridin-2-yl]morpholine

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

A stirred solution of 4-(5-chloro-3-nitropyridin-2-yl)morpholine (500 mg, 2.05 mmol), thiomorpholine 1,1-dioxide (333 mg, 2.46 mmol), Pd2dba3 (94 mg, 0.10 mmol), X-Phos (98 mg, 0.20 mmol), sodium tert-butoxide (394 mg, 4.1 mmol) in toluene (19.7 mL, 184.7 mmol) was heated at reflux for 14 h. After this time the reaction was cooled to rt and partitioned between EtOAc (100 mL) and NaHCO3 (satd aq. solution, 50 mL). The separated organic layer was washed with brine (50 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 1:1) gave 4-[5-(1,1-dioxidothiomorpholin-4-yl)-3-nitropyridin-2-yl]morpholine.

後処理

  1. temperatureat reflux for 14 h
  2. custompartitioned between EtOAc (100 mL) and NaHCO3 (satd aq. solution, 50 mL)
  3. washThe separated organic layer was washed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-845f7dfe42174b5dbd81a64dd0442b68
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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