Water → HCID 66795622, compound

HRID 1944818Notes

Reaction equation

HRID 1944818 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH2:23][NH:24][C:25]2[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=2[CH:34]([CH3:36])[CH3:35])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Li][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1.O>CCOCC>[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[NH:24][C:25]2[C:30]([CH:31]([CH3:32])[CH3:33])=[CH:29][CH:28]=[CH:27][C:26]=2[CH:34]([CH3:36])[CH3:35])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 66796016HCID 66796016, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 66795622HCID 66795622, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2.35 g (4.90 mmol) of N-[(6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridin-2-yl) methyl]-2,6-diisopropylaniline in 50 ml of THF 20.0 ml (14.8 mmol) of 0.74 M PhLi in ether was added by vigorous stirring at −78° C. The reaction mixture was heated to room temperature and stirred for 10 minutes. Further on, 2 ml of water was added, and the resulting mixture was poured into 50 ml of water. The crude product was extracted with 3×30 ml of ether. The organic extract was washed by 2×50 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: dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 2.38 g (86%) of orange oil. Anal. calc. for C39H45N3: C, 84.28; H, 8.16; N, 7.56. Found: C, 84.41; H, 8.17; N, 7.38. For 1H NMR (in CDCl3) see FIG. 1—Bottom spectrum.

Workup

  1. temperatureThe reaction mixture was heated to room temperature
  2. stirringstirred for 10 minutes
  3. extractionThe crude product was extracted with 3×30 ml of ether
  4. extractionThe organic extract
  5. washwas washed by 2×50 ml of water
  6. dry with materialdried over K2CO3
  7. customevaporated to dryness
  8. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.)

Sources & evidence

ORD record
ord-a8b6e50b26564c26b0d0a43c7b00a095
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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