Diethyl Ether → Methyl 3-azido-6-bromo-2-(3-chloro-4-methoxyphenyl)isonicotinate

HRID 2410729

반응식

HRID 2410729 반응식
[NH2:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([Cl:20])[CH:13]=2)=[N:10][C:9]([Br:21])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N([O-])=O.[Na+].[N-:26]=[N+:27]=[N-].[Na+].C(OCC)C>FC(F)(F)C(O)=O>[N:1]([C:2]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([Cl:20])[CH:13]=2)=[N:10][C:9]([Br:21])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[N+:26]=[N-:27]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 86663013Methyl 3-amino-6-bromo-2-(3-chloro-4-methoxyphenyl)isonicotinate

생성물 1

HCID 86663014Methyl 3-azido-6-bromo-2-(3-chloro-4-methoxyphenyl)isonicotinate

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

Methyl 3-amino-6-bromo-2-(3-chloro-4-methoxyphenyl)isonicotinate (181 mg, 0.487 mmol) was dissolved in trifluoroacetic acid (2.4 mL) and cooled in an ice bath. Solid sodium nitrite (67 mg, 0.97 mmol) was added with stirring to give a dark red mixture. After 10 minutes, solid sodium azide (317 mg, 4.87 mmol) was added followed by diethyl ether (2.4 mL). This was stirred in the ice bath for 10 minutes and then partitioned between EtOAc and sufficient saturated aqueous NaHCO3 solution (gas evolution) to neutralize the acid. The organic phase was separated, washed with brine, dried with sodium sulfate, and the solvent removed. The gave methyl 3-azido-6-bromo-2-(3-chloro-4-methoxyphenyl)isonicotinate (161 mg) as a yellow solid. MS (ESI) m/z 398.9 (M+H). 1H NMR (CDCl3) δ ppm 7.85 (1H, d, J=2.14 Hz), 7.75 (1H, s), 7.71 (1H, dd, J=8.55, 2.14 Hz), 7.01 (1H, d, J=8.55 Hz), 4.01 (3H, s), 3.96 (3H, s).

후처리

  1. temperaturecooled in an ice bath
  2. customto give a dark red mixture
  3. custompartitioned between EtOAc and sufficient saturated aqueous NaHCO3 solution (gas evolution)
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried with sodium sulfate
  7. customthe solvent removed

출처 및 근거

ORD 기록
ord-1d3959e7e18f45a1bd0d283fbde8d73b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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