2-Pyridinecarboxaldehyde → HCID 86675199, compound

HRID 1503570Notes

Reaction equation

HRID 1503570 reaction equation
[F:1][C:2]([F:28])([F:27])[CH:3]([C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=1)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]=O.[BH4-].[Na+]>CO>[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][NH:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[CH:3]([C:18]2[CH:19]=[C:20]([Cl:26])[C:21]([Cl:25])=[C:22]([Cl:24])[CH:23]=2)[C:2]([F:1])([F:27])[F:28])=[CH:7][C:8]=1[C:14]([F:16])([F:17])[F:15]

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 86675200HCID 86675200, compound

Product 1

HCID 86675199HCID 86675199, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-(4-(4,4,4-Trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)-2-(trifluoromethyl)phenyl)methanamine (0.46 g, 1 mmol) was dissolved in CH3OH (3 mL). To this was added pyridine-2-carbaldehyde (0.107 g, 1 mmol). The reaction mixture was stirred for 1 h. After 1 h, NaBH4 (0.076 g, 2 mmol) was added and left at ambient temperature for 3 h. The reaction mixture was concentrated to give an oily residue. Purification by flash column chromatography (SiO2, 100-200 mesh; 30-50% EtOAc in hexane) afforded the title compound as a pale yellow liquid (0.22 g, 40%): 1H NMR (400 MHz, CDCl3) δ 8.58 (d, J=4.8 Hz, 1H), 7.74 (m, 1H), 7.62 (m, 2H), 7.52 (m, 1H), 7.4 (s, 2H), 7.3 (m, 1H), 7.2 (m, 2H), 6.60 (d, J=16.0 Hz, 1H), 6.38 (dd, J=16.0, 8.0 Hz, 1H), 4.10 (m, 1H), 4.02 (s, 2H), 3.96 (s, 2H); ESIMS m/z 552.95 ([M+H]+); IR (thin film) 3338, 1114, 808 cm−1.

Workup

  1. waitAfter 1 h
  2. waitleft at ambient temperature for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. customto give an oily residue
  5. customPurification by flash column chromatography (SiO2, 100-200 mesh; 30-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-e5c9b7b2394f47de92dbdc21b1d684a5
Source dataset
uspto-grants-2015_12
Patent number
US09212163B2

Reaction notes

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