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

HRID 1427471
Notes
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Reaction equation

HRID 1427471 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fe263ae3d6f54f9d8feac645b7fb5d8d
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933104B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes