Tetrahydrofuran → 6-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile

HRID 81065노트

반응식

HRID 81065 반응식
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[N:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[CH:3]=1.[Cl-].[NH4+].C1COCC1>[Zn].CO>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([C:8]#[N:9])=[C:6]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:12][CH:11]=3)[N:5]=2)=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 669270004-Chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile

생성물 1

HCID 669269446-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile수율 40.2%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

A mixture of 4-chloro-6-(4-nitrophenyl)-2-(4-phenoxyphenyl)nicotinonitrile (136.3 mg, 0.319 mmol), zinc dust (312 mg, 4.78 mmol), ammonium chloride (256 mg, 4.78 mmol), THF (3 mL) and methanol (3 mL) was stirred at room temperature for 15 min, and filtered. The filtrate was concentrated and partitioned with dichloromethane and saturated sodium bicarbonate. The organic layer was separated and concentrated. Silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes, gave pure 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile as yellow solid (51 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.96-8.04 (4H, m), 7.70 (1H, s), 7.40 (2H, t, J=8.03 Hz), 7.18 (1H, t, J=7.40 Hz), 7.08-7.14 (4H, m), 6.76 (2H, δ, J=8.78 Hz), 4.04 (2H, s); MS (ES+) m/z: 398 (M+H); LC retention time: 4.551 min (analytical HPLC Method A). Additional impure product was also obtained from the chromatography (48.1 mg).

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompartitioned with dichloromethane and saturated sodium bicarbonate
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. washSilica gel chromatography, eluting with 0-40% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-509b039825f144e680a55a26c46d6e35
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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