반응 #2469082

반응 방정식

5-Fluoro-3-methyl-indol-1-ylamine

4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid

HOTT

DIPEA

→

4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)amide

수율 36.3%

용매

water

EtOAc

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture is stirred at rt overnight
2. 2
   기타The organic phase is separated
3. 3
   세척washed with saturated aqueous NaHCO3, water and brine
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue is purified by silica gel chromatography
8. 8
   세척eluting with 60% EtOAc in heptane

실험 절차

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (335 mg, 1.56 mmol), HOTT (638 mg, 1.72 mmol), and DIPEA) (700 μL, 4.01 mmol in DMF (6 mL) is stirred stirred at rt under N2 for 20 min. 5-Fluoro-3-methyl-indol-1-ylamine (241 mg, 1.47 mmol) is added. The resulting mixture is stirred at rt overnight. The mixture is portioned between EtOAc and water. The organic phase is separated, washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 60% EtOAc in heptane to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)amide (193 mg, 36%) as a solid. MS: 362 (M+H). 1H NMR (300 MHz, CDCl3): δ 10.41 (s, 1H), 8.84 (s, 1H), 8.55 (s, 1H), 8.48-8.45 (m, 1H), 7.86 (t, 1H), 7.40-7.36 (m, 1H), 7.24-7.20 (m, 2H), 7.05-7.01 (m, 2H), 2.82 (s, 3H), 2.32 (s, 3H).

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