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

HRID 634073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634073
C([O-])([O-])=O.[Na+].[Na+].O.[CH3:8][C:9]1[CH:32]=[CH:31][CH:30]=[CH:29][C:10]=1[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1B1OC(C)(C)C(C)(C)O1.Br[C:34]1[N:39]=[C:38]([CH2:40][NH:41][C:42]2[C:47]([CH:48]([CH3:50])[CH3:49])=[CH:46][CH:45]=[CH:44][C:43]=2[CH:51]([CH3:53])[CH3:52])[CH:37]=[CH:36][CH:35]=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>[CH:51]([C:43]1[CH:44]=[CH:45][CH:46]=[C:47]([CH:48]([CH3:50])[CH3:49])[C:42]=1[NH:41][CH2:40][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([C:14]2[C:13]([CH2:12][NH:11][C:10]3[CH:29]=[CH:30][CH:31]=[CH:32][C:9]=3[CH3:8])=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:19])[N:39]=1)([CH3:53])[CH3:52]

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 90311811N-[(6-Bromopyridin-2-yl)methyl]-2,6-diisopropylanilineHCID 1317354812-Methyl-N-[3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]aniline

Produkt 1

HCID 1176529572,6-Diisopropyl-N-{[6-(2-methyl-6-{[(2-methylphenyl)amino]methyl}phenyl)pyridin-2-yl]methyl}aniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 5.50 g (19 mmol) of Na2CO3×10H2O, 100 ml of water and 30 ml of methanol was purged with argon for 30 min. The obtained solution was added to a mixture of 2.60 g (7.7 mmol) of 2-methyl-N-[3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]aniline, 2.68 g (7.7 mmol) of N-[(6-bromopyridin-2-yl)methyl]-2,6-diisopropylaniline, and 0.44 g (0.39 mmol) of Pd(PPh3)4 in 120 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 purified by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-triethylamine=20:1, vol.). Yield 2.10 g (57%) of white crystalline solid. Anal. calc. for C33H39N3: C, 82.97; H, 8.23; N, 8.80. Found: C, 83.19; H, 8.45; N, 8.62. 1H NMR (CDCl3): δ 7.71 (m, 1H), 7.37 (m, 1H), 7.28-7.32 (m, 2H), 7.22-7.26 (m, 2H), 7.00-7.13 (m, 5H), 6.61 (m, 1H), 6.47 (m, 1H), 4.25 (s, 2H), 4.10 (s, 2H), 3.98 (br.s, 1H), 3.82 (br.s, 1H), 3.31 (s, J=6.9 Hz, 2H), 2.14 (s, 3H), 2.09 (s, 3H), 1.21 (d, J=6.9 Hz, 12H).

Aufarbeitung

  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 purified by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-triethylamine=20:1, vol.)

Quellen und Nachweise

ORD-Eintrag
ord-01b65ee2d5e74a7cbf2fb9fdbc581fd1
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321858B2

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