Potassium Carbonate → 6-Amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile

HRID 1795388ノート

反応式

HRID 1795388 の反応式
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](I)[C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.B([O-])O[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].O.C1COCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[CH:3]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 155382846-Amino-2-iodo-3,4-dimethoxybenzonitrileHCID 178514833HCID 178514833、化合物

生成物 1

HCID 99430356-Amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile収率 89.8%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Under nitrogen, to anhydrous THF (1000 ml) was added 6-amino-2-iodo-3,4-dimethoxybenzonitrile (see Example 1, 50.0 g, 164 mmol), Pd(OAc)2 (1.85 g, 8.22 mmol), PPh3 (triphenylphosphine, 4.31 g, 16.4 mmol), THF wet boronate [from step (a), 286 g, 493 mmol], Cul (12.5 g, 65 mmol) and K2CO3 (45.5 g, 328 mmol). The reaction mixture was then stirred at reflux for 16 hours. After this time, the reaction mixture was cooled to room temperature and water (1000 ml) added. The mixture was then filtered through an Arbocel™ filter aid pad and the pad washed with THF (500 ml). The filtrate was then extracted with CH2Cl2 (1000 ml). The aqueous phase was back extracted with CH2Cl2 (500 ml) and the combined CH2Cl2 extracts were evaporated in vacuo to yield the crude product as a dark brown solid. Recrystallisation from EtOAc (250 ml) afforded 37.6 g (87%) of the title compound as a beige solid.

後処理

  1. temperatureat reflux for 16 hours
  2. filtrationThe mixture was then filtered through an Arbocel™
  3. filtrationfilter aid pad
  4. washthe pad washed with THF (500 ml)
  5. extractionThe filtrate was then extracted with CH2Cl2 (1000 ml)
  6. extractionThe aqueous phase was back extracted with CH2Cl2 (500 ml)
  7. customthe combined CH2Cl2 extracts were evaporated in vacuo
  8. customto yield the crude product as a dark brown solid
  9. customRecrystallisation from EtOAc (250 ml)

出典と根拠

ORDレコード
ord-594d3071835b415ba8ec4c408424235c
出典データセット
uspto-grants-2006_04
特許番号
US07026479B2

反応ノート

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