Acetonitrile → 4-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehyde

HRID 1427471ノート

反応式

HRID 1427471 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[F:12][C:13]([F:46])([F:45])[C:14]1[CH:19]=[CH:18][C:17](C2N=CC(NC(C3C=CC(C(NCCC(O)=O)=O)=CC=3)CCC)=CN=2)=C[CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].C(#[N:55])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:12][C:13]([F:46])([F:45])[C:14]1[CH:19]=[CH:18][C:17]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)=[N:55][CH:15]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 679808383-(4-(1-(2-(4-(Trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzamido)propanoic acid

生成物 1

HCID 27633594-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehyde

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

実験手順

To a solution of 4-formylphenylboronic acid (100 g, 0.67 mol) and 2-chloro-5-(trifluoromethyl)pyridine 2 (121 g, 0.67 mol) in acetonitrile (900 mL) was added Pd(dppf)Cl2 (24 g, 33.5 mmol) and 2M aqueous Na2CO3 (837 mL). The resulting mixture was heated at reflux for 3 h under nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate (3*500 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give 4-(5-(trifluoromethyl)pyridin-2-yl)benzaldehyde (115 g) as a light yellow solid. 1H NMR (400 MHz CDCl3) δ10.04 (s, 1H), 8.92 (s, 1H), 8.15 (d, J=8.0 Hz, 2H), 7.98 (d, J=8.0 Hz, 1H), 7.96 (d, J=8.0 Hz, 2H), 7.86 (d, J=8.0 Hz, 1H). MS (M+1)=252.0.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 h under nitrogen atmosphere
  3. extractionThe reaction mixture was extracted with ethyl acetate (3*500 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-fe263ae3d6f54f9d8feac645b7fb5d8d
出典データセット
uspto-grants-2015_01
特許番号
US08933104B2

反応ノート

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