Triethylamine → Benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester

HRID 426227노트

반응식

HRID 426227 반응식
Cl[C:2]1[C:3]([F:20])=[N:4][C:5]([F:19])=[C:6]([F:18])[C:7]=1[CH2:8][O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>[Pd].C(O)C>[F:19][C:5]1[C:6]([F:18])=[C:7]([CH2:8][O:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[C:3]([F:20])[N:4]=1

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 59184703Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester

생성물 1

HCID 59184767Benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester수율 85.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester (4.52 g, 15 mmol), anhydrous ethanol (50 ml), 10% palladium on carbon (500 mg), and triethylamine (2.5 ml, 18 mmol) were placed into a 500 ml bottle. The mixture was hydrogenated under hydrogen atmosphere (50 psi) for 1.5 hr. The reaction mixture was filtered through celite pad and the pad was washed with ethanol. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:15)) to afford 3.43 g (85%) of benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester as a white solid. m.p. 73-76° C.; 1H NMR (200 MHz, CDCl3) δ 5.52 (2H, s), 6.95 (1H, m), 7.30-7.70 (3H, m), 8.09-8.15 (2H, m).

후처리

  1. customfor 1.5 hr
  2. filtrationThe reaction mixture was filtered through celite pad
  3. washthe pad was washed with ethanol
  4. customThe combined filtrate was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:15))

출처 및 근거

ORD 기록
ord-3c8e0d5ac3ed4e4d94001b05d4a9f075
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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