Acetic Acid → HCID 58154577, compound

HRID 2359399Notes

Reaction equation

HRID 2359399 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([NH2:19])[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=O)[CH:23]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:19][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[N:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=2)[CH:18]=[CH:17]3)[CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 103713-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58154702HCID 58154702, compound

Product 1

HCID 58154577HCID 58154577, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-(3-(trifluoromethyl)phenyl)quinolin-8-amine (200 mg, 0.7 mmol), 3-pyridinecarbaldehyde (150 mg, 1.4 mmol) and acetic acid (84 mg, 1.4 mmol) in methanol (10 mL) was added NaCNBH3 (88 mg, 1.4 mmol) in portions at room temperature, then the reaction was stirred at room temperature for 5 h. The reaction was concentrated in vacuo, the residue was taken up in DCM, The solution was washed with water (1×50 mL), treated with active carbon and Na2SO4, filtered through a silica gel pad, and the pad was washed with CH2Cl2. The organic solutions were combined and concentrated in vacuo, triturated with a mixture of ethyl acetate/pentane and filtered to give N-(pyridin-3-ylmethyl)-2-(3-(trifluoromethyl)phenyl)quinolin-8-amine as a yellow solid (220 mg, yield 83%) MS (ESI) calcd for C22H16F3N3 (m/z): 379.13. found: 380 [M+1].

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washThe solution was washed with water (1×50 mL)
  3. additiontreated with active carbon and Na2SO4
  4. filtrationfiltered through a silica gel pad
  5. washthe pad was washed with CH2Cl2
  6. concentrationconcentrated in vacuo
  7. customtriturated with a mixture of ethyl acetate/pentane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6e77926fae3d422481efb3071c96efaf
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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