Toluene → HCID 21948853, compound

HRID 2054952Notes

Reaction equation

HRID 2054952 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:7]=1.[NH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27]([CH3:33])=[N:28]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C1(C)C=CC=CC=1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:18])([CH3:19])[CH2:9][C:10]([C:13]([F:14])([F:16])[F:15])([OH:17])[CH2:11][NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][C:27]([CH3:33])=[N:28]3)[CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 1486835-Quinolinamine, 2-methyl-HCID 5049666Sodium triacetoxyborohydride2×HCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Product 1

HCID 21948853HCID 21948853, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 mg (0.97 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 184 mg (1.16 mmol) of 5-amino-2-methylquinoline are heated in 10 ml of acetic acid over 6 hours to 125° C. After cooling to room temperature, it is mixed with 320 mg (1.51 mmol) of sodium triacetoxy borohydride, and it is allowed to stir for 16 hours. After the addition of another 320 mg (1.51 mmol) of sodium triacetoxy borohydride and 2 hours of stirring, toluene is added, and it is concentrated by evaporation in a vacuum. The residue is taken up in ethyl acetate, the organic phase is washed with saturated sodium bicarbonate and saturated sodium chloride solution, and it is dried on sodium sulfate. After chromatography on silica gel with hexane-ethyl acetate (0-60%), 221 mg of the product is obtained.

Workup

  1. stirringof stirring
  2. concentrationit is concentrated by evaporation in a vacuum
  3. washthe organic phase is washed with saturated sodium bicarbonate and saturated sodium chloride solution, and it
  4. customis dried on sodium sulfate

Sources & evidence

ORD record
ord-259b09709da9427f931fe17520481bf5
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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