반응 #46228

반응 방정식

5-bromo-pyridin-2-ylamine

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid

Thionyl chloride

N,N-dimethylformamide

→

product

수율 83.3%

1-(Benzo[d][1,3]dioxol-5-yl)-N-(5-bromopyridin-2-yl)cyclopropane-carboxamide

수율 83.3%

용매

pyridine

반응 조건

후처리

1. 1
   기타The excess thionyl chloride was removed under vacuum
2. 2
   workup.STIRRINGto stir for 15 hours at 110° C
3. 3
   기타The mixture was then evaporated to dryness
4. 4
   세척washed with three 25 mL portions of 1N NaOH
5. 5
   건조The organic layer was dried over sodium sulfate
6. 6
   기타evaporated
7. 7
   기타purified by silica gel column chromatography

실험 절차

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid (2.38 g, 11.5 mmol) was placed in an oven-dried flask under nitrogen. Thionyl chloride (2.5 mL) and N,N-dimethylformamide (0.3 mL) were added and the solution was allowed to stir for 30 minutes at 60° C. The excess thionyl chloride was removed under vacuum and the resulting solid was suspended in 7 mL of anhydrous pyridine. This solution was then slowly added to a solution of 5-bromo-pyridin-2-ylamine (2.00 g, 11.6 mmol) suspended in 10 mL of anhydrous pyridine. The resulting mixture was allowed to stir for 15 hours at 110° C. The mixture was then evaporated to dryness, suspended in 100 mL of dichloromethane, and washed with three 25 mL portions of 1N NaOH. The organic layer was dried over sodium sulfate, evaporated to near dryness, and then purified by silica gel column chromatography utilizing dichloromethane as the eluent to yield the pure product (3.46 g, 83%) ESI-MS m/z calc. 361.2. found 362.1 (M+1)+; Retention time 3.40 minutes. 1H NMR (400 MHz, DMSO-d6) δ 1.06-1.21 (m, 2H), 1.44-1.51 (m, 2H), 6.07 (s, 2H), 6.93-7.02 (m, 2H), 7.10 (d, J=1.6 Hz, 1H), 8.02 (d, J=1.6 Hz, 2H), 8.34 (s, 1H), 8.45 (s, 1H).

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