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

HRID 634052
ノート
印刷プレビュー

反応式

HRID 634052 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒
HCID 887Methanol溶媒
HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-9033fe82485e47b1b2e9fa737888bbd8
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321858B2

反応ノート

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