Water → 2,6-Diisopropyl-N-[[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl](phenyl)methyl]aniline

HRID 1944828Notes

Reaction equation

HRID 1944828 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][C:22]=2[CH2:31][NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[N:16]=1)([CH3:3])[CH3:2].C1COCC1.[Li][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1.O>CCOCC>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=1[NH:13][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][C:22]=2[CH2:31][NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[N:16]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 66799583(2,6-Diisopropylphenyl){[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amineHCID 178506676HCID 178506676, compound

Product 1

HCID 667957402,6-Diisopropyl-N-[[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl](phenyl)methyl]aniline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1.30 g (2.54 mmol) of (2,6-diisopropylphenyl){[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine in 20 ml of THF 8.60 ml (6.35 mmol) of 0.74 M PhLi in ether was added by vigorous stirring at −78° C. The reaction mixture was stirred for 10 minutes at room temperature, then 2 ml of water was added, and, finally, this mixture was poured into 50 ml of water. The product was extracted with 3×20 ml of ether. The organic extract was washed by 2×30 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.). Yield 1.30 g (86%) of yellow oil which crystallized at room temperature. Anal. calc. for C42H43N3: C, 85.53; H, 7.35; N, 7.12. Found: C, 85.72; H, 7.39; N, 6.95. For 1H NMR (in CDCl3) see FIG. 3—Top spectrum.

Workup

  1. stirringThe reaction mixture was stirred for 10 minutes at room temperature
  2. extractionThe product was extracted with 3×20 ml of ether
  3. extractionThe organic extract
  4. washwas washed by 2×30 ml of water
  5. dry with materialdried over K2CO3
  6. customevaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.)
  8. customYield 1.30 g (86%) of yellow oil which crystallized at room temperature

Sources & evidence

ORD record
ord-8527271ed48f4100b607aa6d7674996d
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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