Trifluoroacetic acid → HCID 66926921, compound

HRID 81032Notes

Reaction equation

HRID 81032 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:16]=[N:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH:23](O)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[C:10]=1[C:11]#[N:12].C([SiH](CC)CC)C>ClCCl>[CH2:23]([C:20]1[CH:19]=[CH:18][C:17]([C:13]2[CH:14]=[N:15][CH:16]=[C:9]([Cl:8])[C:10]=2[C:11]#[N:12])=[CH:22][CH:21]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 669270213-Chloro-5-(4-(hydroxy(phenyl)methyl)phenyl)isonicotinonitrile

Product 1

HCID 66926921HCID 66926921, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL, 64.9 mmol) was added to a solution of 3-chloro-5-(4-(hydroxy(phenyl)methyl)phenyl)isonicotinonitrile (327 mg, 0.816 mmol, 80% pure) and triethylsilane (5 mL, 31.3 mmol) in dichloromethane (10 mL). After 1 h at room temperature, the mixture was concentrated, quenched with saturated sodium bicarbonate (30 mL) and extracted with dichloromethane (3×15 mL). The combined extracts were dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 10-30% ethyl acetate in hexanes, gave 3-(4-benzylphenyl)-5-chloroisonicotinonitrile as colorless liquid (195.2 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (1H, s), 8.68 (1H, s), 7.45-7.58 (2H, m), 7.28-7.43 (4H, m), 7.15-7.28 (3H, m), 4.07 (2H, s). MS (ES+) m/z: 305 (M−H2O+H); LC retention time: 4.391 min (analytical HPLC Method A).

Workup

  1. concentrationthe mixture was concentrated
  2. customquenched with saturated sodium bicarbonate (30 mL)
  3. extractionextracted with dichloromethane (3×15 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. washeluting with 10-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0a333da88bdb4087a9961ebf4b51335c
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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