Toluene → 4-(3-Nitro-5-thiomorpholinopyridin-2-yl)morpholine

HRID 1431258노트

반응식

HRID 1431258 반응식
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.C1(C)C=CC=CC=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.[K+].[NH:64]1[CH2:69][CH2:68][S:67][CH2:66][CH2:65]1>CCOC(C)=O.O.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]>[N+:14]([C:4]1[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([N:64]2[CH2:69][CH2:68][S:67][CH2:66][CH2:65]2)[CH:3]=1)([O-:16])=[O:15]

참가 물질

9

반응물 5

HCID 1140TolueneHCID 67164ThiomorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23665647Potassium tert-butoxideHCID 596312064-(5-Chloro-3-nitropyridin-2-yl)morpholine

생성물 1

HCID 596312804-(3-Nitro-5-thiomorpholinopyridin-2-yl)morpholine

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
115 °C

실험 절차

A stirred solution of 4-(5-chloro-3-nitropyridin-2-yl)morpholine (400 mg, 1.64 mmol) in toluene (15.7 mL, 147.7 mmol) was treated with Pd2dba3 (75 mg, 0.082 mmol), X-Phos (78 mg, 0.16 mmol), potassium tert butoxide (368 mg, 3.28 mmol) and thiomorpholine (203 mg, 1.97 mmol). The reaction was heated at 115° C. overnight. After this time the reaction was cooled to rt and diluted with EtOAc (100 mL) and water (50 mL). The separated organic layer was washed with NaHCO3 (satd aq. solution, 40 mL), brine (40 mL) and then dried over magnesium sulfate, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 1:2) gave 4-(3-nitro-5-thiomorpholinopyridin-2-yl)morpholine as a red oil. Mass Spectrum (ESI) m/e=311.2 (M+1).

후처리

  1. temperatureAfter this time the reaction was cooled to rt
  2. washThe separated organic layer was washed with NaHCO3 (satd aq. solution, 40 mL), brine (40 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-83602b98774c44c5ad10d40c24bdc3f3
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940724B2

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