6-Bromopyridine-2-carbaldehyde → 6-{2-[(Mesitylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde

HRID 2370667ノート

反応式

HRID 2370667 の反応式
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[C:12]=1[NH:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]=1B1OC(C)(C)C(C)(C)O1.ClCCl.C(OCC)(=O)C>CO.O.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>[C:11]1([CH3:10])[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[C:12]=1[NH:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]=1[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 3

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 21226138Dichloromethane ethylacetateHCID 667957632,4,6-Trimethyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline

生成物 1

HCID 866601036-{2-[(Mesitylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of 32.4 g (113 mmol) of Na2CO3(H2O)10 in a mixture of 180 ml of methanol and 600 ml of water was added to a mixture of 8.37 g (45.0 mmol) of 6-bromopyridine-2-carbaldehyde, 18.1 g (45.0 mmol) of 2,4,6-trimethyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline and 2.65 g (2.30 mmol) of Pd(PPh3)4 in 600 ml of toluene by vigorous stirring at room temperature. The resulting mixture was stirred at 80° C. for 12 h. Thereafter, this mixture was cooled to room temperature, the organic layer was separated, dried over MgSO4, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-ethyl acetate=100:1 and then 10:1, vol.). Yield 10.7 g (63%). Anal. calc. for C26H24N2O: C, 82.07; H, 6.36; N, 7.36. Found: C, 82.24; H, 6.49; N, 7.18. 1H NMR (CDCl3): 10.12 (s, 1H, CHO), 8.06 (m, 1H, 3-H in Py), 7.90-7.99 (m, 3H, 5,7,8-H in naphthyl), 7.63 (d, J=8.3 Hz, 4-H in naphthyl), 7.54 (m, 1H, 5-H in Py), 7.49 (m, 1H, 4-H in Py), 7.39 (m, 1H, 6-H in naphthyl), 7.28 (d, J=8.3 Hz, 3-H in naphthyl), 6.74 (s, 2H, 3,5-H in mesityl), 3.98 (d, J=13.1 Hz, 1H, CHH′N), 3.89 (d, J=13.1 Hz, 1H, CHH′N), 3.37 (br.s, 1H, NH), 2.20 (s, 3H, 4-Me in mesityl), 2.04 (s, 6H, 2,6-Me in mesityl).

後処理

  1. stirringThe resulting mixture was stirred at 80° C. for 12 h
  2. temperatureThereafter, this mixture was cooled to room temperature
  3. customthe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um

出典と根拠

ORDレコード
ord-be96d279161f455eaa017a87f31c7e49
出典データセット
uspto-grants-2014_04
特許番号
US08710163B2

反応ノート

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