Pyridine → 2-Cyclopentyl-6-methoxy-isonicotinonitrile

HRID 2278770ノート

反応式

HRID 2278770 の反応式
N1C=CC=CC=1.[CH:7]1([C:12]2[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH3:22])[N:20]=2)[C:15]([NH2:17])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH:7]1([C:12]2[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH3:22])[N:20]=2)[C:15]#[N:17])[CH2:8][CH2:9][CH2:10][CH2:11]1

参加物

5

反応物 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 674914362-Cyclopentyl-6-methoxy-isonicotinamide

生成物 1

HCID 674912332-Cyclopentyl-6-methoxy-isonicotinonitrile収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Pyridine (8.86 g, 91.3 mmol) is added to a solution of 2-cyclopentyl-6-methoxy-isonicotinamide (3.35 g, 15.2 mmol) in DCM (100 mL). The mixture is cooled to 0° C. before trifluoroacetic acid anhydride (9.58 g, 45.6 mmol) is added portionwise. The mixture is stirred at 0° C. for 1 h before it is diluted with DCM (100 mL) and washed with sat. aq. NaHCO3 solution (100 mL) and brine (100 mL). The separated org. phase is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-cyclopentyl-6-methoxy-isonicotinonitrile (2.09 g) as a pale yellow oil; LC-MS**: tR=0.80 min, [M+1]+=not detectable; 1H NMR (D6-DMSO): δ 1.61-1.82 (m, 6H), 1.94-2.03 (m, 2H), 3.16 (quint, J=7.8 Hz, 1H), 3.89 (s, 3H), 7.15 (s, 1H), 7.28 (s, 1H).

後処理

  1. additionis added portionwise
  2. washwashed with sat. aq. NaHCO3 solution (100 mL) and brine (100 mL)
  3. dry with materialphase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

出典と根拠

ORDレコード
ord-37cf1f27ae884913a17d42d7a16de1fc
出典データセット
uspto-grants-2015_09
特許番号
US09133179B2

反応ノート

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