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

HRID 1878632

反応式

HRID 1878632 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-91b69fd51ec14050860577b9e1cd9ae3
出典データセット
uspto-grants-2012_11
特許番号
US08314120B2

関連ノート

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