Trifluoroacetic anhydride → 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]-5-cyanopyridine

HRID 1455994노트

반응식

HRID 1455994 반응식
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:19]([CH:33]=1)[CH2:20][N:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([NH2:32])=O)=[CH:26][N:25]=1)[CH2:22][CH3:23]>N1C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:19]([CH:33]=1)[CH2:20][N:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:32])=[CH:26][N:25]=1)[CH2:22][CH3:23]

참가 물질

6

반응물 2

HCID 9845Trifluoroacetic anhydrideHCID 221056502-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxamide

생성물 1

HCID 221056452-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]-5-cyanopyridine수율 80.4%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Trifluoroacetic anhydride (0.51 ml) was added dropwise to a mixture of 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxamide (1.05 g) in pyridine (0.58 ml) and THF (20 ml) at 20° C. The mixture was stirred at ambient temperature for 18 hours, diluted with ethyl acetate, washed with water, saturated aqueous NaHCO3 and brine, and dried (MgSO4). The solvent was evaporated and the residue purified by MPLC, eluting with dichloromethane/methanol mixtures (100:0 to 95:5) to give 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]-5-cyanopyridine (0.81 g) as a gum.

후처리

  1. washwashed with water, saturated aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customthe residue purified by MPLC
  5. washeluting with dichloromethane/methanol mixtures (100:0 to 95:5)

출처 및 근거

ORD 기록
ord-d00d01872da44982a41d6751e17fb0a6
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843942

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