Tetrahydrofuran → 1-(4-fluorobenzyl)-5-phenyl-1H-pyrrole-2-carboxylic acid methoxy-methylamide

HRID 381500노트

반응식

HRID 381500 반응식
CO[CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)=[O:6].C1C[O:21][CH2:20]C1.[H-].[Na+].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>CCOC(C)=O>[CH3:20][O:21][N:4]([CH3:3])[C:5]([C:7]1[N:8]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=2)[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)=[O:6]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 544094405-phenyl-1H-pyrrole-2-carboxylic acid methoxymethylamide

생성물 1

HCID 206968041-(4-fluorobenzyl)-5-phenyl-1H-pyrrole-2-carboxylic acid methoxy-methylamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a 100 mL round bottomed flask containing 5-phenyl-1H-pyrrole-2-carboxylic acid methoxymethylamide AV-6-1 (0.692 g, 3.01 mmol) was added a stirring bar and an argon inlet was attached. THF (15 mL) was added and, when all of the solids had dissolved, NaH-oil suspension (0.132 g of a 60% w/w suspension, 3.31 mmol) was added. This mixture was stirred 15 min at ambient temperature then 4-fluorobenzylbromide (0.41 mL, 3.31 mmol) was added. The resulting mixture was stirred 24 h at ambient temperature. The mixture was diluted with EtOAc and the solution was washed with 1N HCl, water and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. This material was chromatographed on silica gel using 25% EtOAc in hexanes a eluant to give 1-(4-fluorobenzyl)-5-phenyl-1H-pyrrole-2-carboxylic acid methoxy-methyl-amide AV-7-1. 1H NMR (CDCl3) δ 3.21 (3H, s), 3.47 (3H, s), 5.52 (2H, s), 6.24 (1H, d, j=3.9 Hz), 6.75 to 6.90 (5H, m), 6.94 (1H, d, j=3.9 Hz), 7.38 (4H, m).

후처리

  1. additionwas added a stirring bar and an argon inlet
  2. dissolutionwhen all of the solids had dissolved
  3. stirringThe resulting mixture was stirred 24 h at ambient temperature
  4. washthe solution was washed with 1N HCl, water and brine
  5. customDrying
  6. filtration(MgSO4), filtration and removal of the solvent in vacuo
  7. customgave an oil
  8. customThis material was chromatographed on silica gel using 25% EtOAc in hexanes a eluant

출처 및 근거

ORD 기록
ord-7b8418e229524a65954b599ae113f6d1
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306891B1

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