반응 #2469084

반응 방정식

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

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

HOTT

DIPEA

→

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

수율 68.2%

용매

water

EtOAc

DMF

반응 조건

후처리

1. 1
   기타The organic phase is separated
2. 2
   세척washed with saturated aqueous NaHCO3, water and brine
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue is purified by silica gel chromatography
7. 7
   세척eluting with 70% EtOAc in heptane

실험 절차

A solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (209 mg, 0.88 mmol), HOTT (435 mg, 1.17 mmol), and DIPEA (400 μL, 2.29 mmol) in DMF (10 mL) is stirred at rt under N2 for 20 min. 5-Fluoro-3-methyl-indol-1-ylamine (125 mg, 0.76 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 70% EtOAc in heptane to afford 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide (180 mg, 68%) as a solid. MS: 348 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 12.12 (s, 1H), 9.47 (s, 2H), 8.82 (d, 1H), 8.51 (d, 1H), 8.05 (td, 1H), 7.62 (dd, 1H), 7.42 (dd, 1H), 7.35 (dd, 1H), 7.33 (s, 1H), 7.03 (td, 1H), 2.27 (s, 3H).

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