Pyridine → Phenyl 6-fluoropyridin-3-ylcarbamate

HRID 218310

반응식

HRID 218310 반응식
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].CCOC(C)=O>C1COCC1>[F:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:16](=[O:17])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 8194405-Amino-2-fluoropyridine

생성물 1

HCID 59313675Phenyl 6-fluoropyridin-3-ylcarbamate수율 101.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-Fluoropyridin-3-amine (224 mg, 2.00 mmol) was dissolved in THF (4 mL). Pyridine (202 μL, 2.50 mmol) was added, followed by phenyl chloroformate (258 μL, 2.06 mmol). The reaction was stirred at rt for 2 h, then EtOAc (20 mL) was added. The reaction was washed with 1 M HCl (10 mL), water (10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL), then dried (MgSO4), filtered, and concentrated in vacuo to give slightly impure 16A (471 mg, >100%). 16A had an analytical HPLC retention time=2.437 min (Phenomenex Luna 3.0×50 mm, 10-90% aqueous MeOH over 5 min containing 0.1% TFA) and a LC/MS M++1=233.

후처리

  1. washThe reaction was washed with 1 M HCl (10 mL), water (10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-45af494887794d2b85dd312bb66f8e4a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198438B2

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