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

HRID 634065Notes

Reaction equation

HRID 634065 reaction equation
C([O-])([O-])=O.[Na+].[Na+].O.[CH3:8][C:9]1[CH:35]=[CH:34][CH:33]=[CH:32][C:10]=1[NH:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1B1OC(C)(C)C(C)(C)O1.Br[C:37]1[N:42]=[C:41]([CH2:43][NH:44][C:45]2[C:50]([CH:51]([CH2:54][CH3:55])[CH2:52][CH3:53])=[CH:49][CH:48]=[CH:47][C:46]=2[CH:56]([CH2:59][CH3:60])[CH2:57][CH3:58])[CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.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.CO>[CH2:57]([CH:56]([C:46]1[CH:47]=[CH:48][CH:49]=[C:50]([CH:51]([CH2:54][CH3:55])[CH2:52][CH3:53])[C:45]=1[NH:44][CH2:43][C:41]1[CH:40]=[CH:39][CH:38]=[C:37]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:21]=[CH:22][C:13]=2[CH2:12][NH:11][C:10]2[CH:32]=[CH:33][CH:34]=[CH:35][C:9]=2[CH3:8])[N:42]=1)[CH2:59][CH3:60])[CH3:58]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 667958502-Methyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}anilineHCID 117652978N-[(6-Bromopyridin-2-yl)methyl]-2,6-bis(1-ethylpropyl)aniline

Product 1

HCID 1176528702,6-Bis(1-ethylpropyl)-N-{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methyl}aniline

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.50 g (6.7 mmol) of Na2CO3×10H2O, 69 ml of water and 22 ml of methanol was purged with argon for 30 min. The obtained solution was added to a mixture of 2.50 g (6.7 mmol) of 2-methyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline, 2.70 g (6.7 mmol) of N-[(6-bromopyridin-2-yl)methyl]-2,6-bis(1-ethylpropyl)aniline, and 0.39 g (0.34 mmol) of Pd(PPh3)4 in 90 ml of toluene. This mixture was stirred for 12 h at 70° C., then cooled to room temperature. The organic layer was separated, the aqueous layer was extracted with 3×50 ml of ethyl acetate. The combined organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was re-crystallized from 5 ml of diethyl ether. Yield 2.20 g (58%) of white crystalline powder. Anal. calc. for C39H45FN3: C, 84.31; H, 8.31; N, 7.37. Found: C, 84.28; H, 8.26; N, 7.19. 1H NMR (CDCl3): δ 7.90 (d, J=8.5 Hz, 1H), 7.88 (m, 1H), 7.83 (m, 1H), 7.66 (d, J=8.5 Hz, 1H), 7.60 (m, 1H), 7.35-7.49 (m, 4H), 6.96-7.07 (m, 5H), 6.61 (m, 1H), 6.53 (m, 1H), 4.17-4.32 (m, 4H), 3.92 (br.m, 1H), 3.85 (br.s, 1H), 2.88 (m, 2H), 2.08 (s, 3H), 1.62 (m, 4H), 1.49 (m, 4H), 0.73 (t, J=7.1 Hz, 6H), 0.71 (t, J=7.1 Hz, 6H).

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 3×50 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 residue was re-crystallized from 5 ml of diethyl ether

Sources & evidence

ORD record
ord-1f5f436347f842279498c738735d8f30
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

Loading…