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

HRID 1944822ノート

反応式

HRID 1944822 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]=[CH:36][CH:35]=[CH:34][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>[CH3:10][C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][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 667958502-Methyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline

生成物 1

HCID 866633926-(2-{[(2-Methylphenyl)amino]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 28.4 g (99.0 mmol) of Na2CO3(H2O)10 in a mixture of 150 ml of methanol and 580 ml of water was added to a mixture of 7.38 g (39.7 mmol) of 6-bromopyridine-2-carbaldehyde, 14.8 g (39.7 mmol) of 2-methyl-N-{ [1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline and 2.29 g (2.00 mmol) of Pd(PPh3)4 in 720 ml of toluene by vigorous stirring at room temperature. The resulting mixture was stirred at 80° C. for 12 h. Further on, 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 20:1). Yield 10.7 g (76%). Anal. calc. for C24H20N2O: C, 81.79; H, 5.72; N, 7.95. Found: C, 81.91; H, 5.80; N, 7.81. 1H NMR (CDCl3): 10.10 (s, 1H, CHO), 8.01-8.05 (m, 2H, 3,4-H in Py), 7.96 (d, J=8.6 Hz, 1H, 4-H in naphthyl), 7.90 (m, 1H, 8-H in naphthyl), 7.68-7.70 (m, 2H, 5-H in Py and 3-H in naphthyl), 7.60 (m, 1H, 7-H in naphthyl), 7.41 (m, 1H, 6-H in naphthyl), 7.81 (m, 1H, 5-H in naphthyl), 7.03 (m, 2H, 3,5-H in Ph), 6.63 (m, 1H, 4-H in Ph), 6.50 (m, 1H, 6-H in Ph), 4.22 (m, 2H, CH2N), 3.93 (br. s, 1H, NH), 2.10 (s, 3H, Me).

後処理

  1. stirringThe resulting mixture was stirred at 80° C. for 12 h
  2. temperatureFurther on, 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-599f6f511c064490add20ce01d6da1d8
出典データセット
uspto-grants-2013_03
特許番号
US08394902B2

反応ノート

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