Dimethylformamide → Ethyl 8-[(2-bromo-5-fluorobenzyl)oxy]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 71128

反応式

HRID 71128 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.[H-].[Na+].[Br:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[CH2:39]Br.[Cl-].[NH4+].CN(C=[O:47])C>>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[CH2:39][O:47][C:23]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:22][CH2:21][CH2:20][N:19]2[C:15]([C:5]3[CH:6]=[CH:7][C:8]([C:9]4[O:13][C:12]([CH3:14])=[N:11][CH:10]=4)=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:16][N:17]=[C:18]12

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 24758Sodium hydride2 回HCID 25517Ammonium ChlorideHCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzeneHCID 66608236Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

生成物 1

HCID 66608314Ethyl 8-[(2-bromo-5-fluorobenzyl)oxy]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

実験手順

To a mixture of ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1000 mg) in DMF (8 mL) was added sodium hydride (60%, 115 mg), and the mixture was stirred at room temperature for 1 hr in the air. Sodium hydride (60%, 115 mg) and 1-bromo-2-(bromomethyl)-4-fluorobenzene (1051 mg) were added, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (920 mg).

後処理

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-a6c11ad867f14aeb9f4a8d1699ce80e3
出典データセット
uspto-grants-2014_09
特許番号
US08822699B2

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