3-Fluorobenzylamine → 3-[(3-Fluorobenzyl)amino]pyridine-4-carboxylic acid

HRID 1847140ノート

反応式

HRID 1847140 の反応式
F[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH2:16]>CC(N(C)C)=O>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH:16][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

参加物

4

反応物 2

HCID 668533-FluorobenzylamineHCID 3453613-Fluoropyridine-4-carboxylic acid

生成物 1

HCID 817504513-[(3-Fluorobenzyl)amino]pyridine-4-carboxylic acid収率 33.2%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
168 °C

実験手順

3-Fluoroisonicotinic acid (100 mg, 0.71 mmol) and 3-fluorobenzylamine (308 μL, 2.84 mmol) were combined in DMA (3 mL) and the solution was stirred at 168° C. in a microwave for 90 min. The solution was concentrated in vacuo and purified through a short plug of silica gel chromatography (20% MeOH/DCM). The semi-pure fractions were concentrated and then taken up in water to give a white precipitate, which was collected by filtration and dried under vacuum to give 58 mg (33%) of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 8.18 (s, 1H), 7.99 (br s, 1H), 7.84 (d, 1H, J=5.0 Hz), 7.58 (d, 1H, J=5.0 Hz), 7.31-7.41 (m, 2H), 7.15-7.23 (m, 2H), 4.62 (s, 2H). [M+H] calc'd for C13H11FN2O2, 247. Found 247.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified through a short plug of silica gel chromatography (20% MeOH/DCM)
  3. concentrationThe semi-pure fractions were concentrated
  4. customto give a white precipitate, which
  5. filtrationwas collected by filtration
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-fc70bb9106b147b09da9613d18c86e88
出典データセット
uspto-grants-2015_02
特許番号
US08952151B2

反応ノート

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