Binap, (A+-)- → 2-Butyl-5-(4-phenylpyridin-3-ylamino)isoindolin-1-one

HRID 1878632

반응식

HRID 1878632 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:60][C:61]1[CH:62]=[C:63]2[C:67](=[CH:68][CH:69]=1)[C:66](=[O:70])[N:65]([CH2:71][CH2:72][CH2:73][CH3:74])[CH2:64]2.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].C(OCC)(=O)C.O>[CH2:71]([N:65]1[CH2:64][C:63]2[C:67](=[CH:68][CH:69]=[C:61]([NH:60][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][C:7]=3[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:62]=2)[C:66]1=[O:70])[CH2:72][CH2:73][CH3:74]

참가 물질

9

반응물 4

HCID 634876Binap, (A+-)-HCID 27629283-Bromo-4-phenylpyridineHCID 23676156Sodium t-butoxideHCID 674320655-Amino-2-butyl-2,3-dihydro-1H-isoindol-1-one

생성물 1

HCID 534771292-Butyl-5-(4-phenylpyridin-3-ylamino)isoindolin-1-one수율 46%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

3-Bromo-4-phenylpyridine (125 mg, 0.534 mmol) was added to a suspension of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (33 mg, 0.053 mmol) and tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (49 mg, 0.053 mmol) in toluene (5 mL). 5-Amino-2-butylisoindolin-1-one (120 mg, 0.587 mmol) and sodium tert-butoxide (128 mg, 1.335 mmol) were added and the mixture was stirred and heated in the microwave (120° C., 300 W, 75 min). Water and ethyl acetate were added, the organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and dried over MgSO4. Purification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol) provided 2-butyl-5-(4-phenylpyridin-3-ylamino)isoindolin-1-one (56 mg, 46%). ESI-MS [M+H]+=358.2.

후처리

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. customPurification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol)

출처 및 근거

ORD 기록
ord-91b69fd51ec14050860577b9e1cd9ae3
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314120B2

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