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

HRID 1455994ノート

反応式

HRID 1455994 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d00d01872da44982a41d6751e17fb0a6
出典データセット
uspto-grants-1998_12
特許番号
US05843942

反応ノート

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