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

HRID 1944822노트

반응식

HRID 1944822 반응식
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

참가 물질

8

반응물 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

생성물 1

HCID 866633926-(2-{[(2-Methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-599f6f511c064490add20ce01d6da1d8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394902B2

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