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Water → N-(1-{6-[2-(Anilinomethyl)-1-naphthyl]pyridin-2-yl}-1-methylethyl)-2,6-diethylaniline

HRID 634052
Notes
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Reaction equation

HRID 634052 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]=2[CH2:19][NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)O1.Br[C:29]1[N:34]=[C:33]([C:35]([NH:38][C:39]2[C:44]([CH2:45][CH3:46])=[CH:43][CH:42]=[CH:41][C:40]=2[CH2:47][CH3:48])([CH3:37])[CH3:36])[CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CO>[NH:20]([CH2:19][C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[C:29]1[N:34]=[C:33]([C:35]([NH:38][C:39]2[C:44]([CH2:45][CH3:46])=[CH:43][CH:42]=[CH:41][C:40]=2[CH2:47][CH3:48])([CH3:37])[CH3:36])[CH:32]=[CH:31][CH:30]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 117652810N-[1-(6-Bromopyridin-2-yl)-1-methylethyl]-2,6-diethylanilineHCID 131735478N-{[1-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}-aniline

Product 1

HCID 117652854N-(1-{6-[2-(Anilinomethyl)-1-naphthyl]pyridin-2-yl}-1-methylethyl)-2,6-diethylaniline

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.17 g (6.00 mmol) of N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}-aniline, 4.33 g (6.00 mmol) of N-[1-(6-bromopyridin-2-yl)-1-methylethyl]-2,6-diethylaniline and 1.60 g (15.10 mmol) of Na2CO3×10H2O, 65 ml of water, 18 ml of methanol and 80 ml of toluene was purged with argon for 30 min. To this solution 0.35 g (0.30 mmol) of Pd(PPh3)4 was added. This mixture was stirred for 12 h at 80° C., then cooled to room temperature. The organic layer was separated, the aqueous layer was extracted with 3×200 ml of ethyl acetate. The combined organic extract was washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel 60 (40-63 um, eluent: dichloromethane-ethyl acetate=20:1, vol.). Yield 2.35 g (76%) of yellow oil. Anal. calc. for C35H37N3: C, 84.13; H, 7.46; N, 8.41. Found: C, 84.34; H, 7.55; N, 8.35. 1H NMR (CDCl3): δ 7.87-7.90 (m, 2H, 4, 8-H in naphtalene), 7.81 (t, J=7.8 Hz, 1H, 4-H in pyridine), 7.70 (dd, J=7.8 Hz, J=0.6 Hz, 1H, 5-H in pyridine), 7.67 (d, J=8.6 Hz, 1H, 3-H in naphtalene), 7.45-7.49 (m, 2H, 5, 7-H in naphtalene), 7.38-7.42 (m, 1H, 6-H in naphtalene), 7.31 (dd, J=7.8 Hz, J=0.6 Hz, 1H, 3-H in pyridine), 7.10 (m, 2H, 3, 5-H in Ph), 6.93-7.00 (m, 3H, 3, 4, 5-H in 2, 6-Et2C6H3), 6.66 (m, 1H, 4-H in Ph), 6.58 (m, 2H, 2, 6-H in Ph), 4.12-4.28 (m, 4H, CH2NH and NHCMe2), 2.44 (q, J=7.6 Hz, 4H, CH2Me), 2.43 (q, J=7.6 Hz, 4H, CH2Me), 1.54 (s, 3H, CMeMe′), 1.44 (s, 3H, CMeMe′), 1.02 (t, J=7.6 Hz, 6H, CH2Me).

Workup

  1. customwas purged with argon for 30 min
  2. temperaturecooled to room temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 3×200 ml of ethyl acetate
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. customThe crude product was purified by flash chromatography on silica gel 60 (40-63 um, eluent: dichloromethane-ethyl acetate=20:1, vol.)

Sources & evidence

ORD record
ord-9033fe82485e47b1b2e9fa737888bbd8
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321858B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes