Carbon tetrabromide → HCID 68528577、化合物

HRID 2247637ノート

反応式

HRID 2247637 の反応式
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]([CH2:26]O)[O:24][CH:25]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:53]1[CH2:56][CH:55]([C:57]([O:59][CH2:60][CH3:61])=[O:58])[CH2:54]1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>ClCCl.O>[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]([CH2:26][N:53]5[CH2:56][CH:55]([C:57]([O:59][CH2:60][CH3:61])=[O:58])[CH2:54]5)[O:24][CH:25]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

9

反応物 6

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 44828820Ethyl azetidine-3-carboxylate hydrochlorideHCID 68525447HCID 68525447、化合物

生成物 1

HCID 68528577HCID 68528577、化合物収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of (4-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-furyl)methanol (0.20 g, 0.50 mmol) that was obtained in Example 1 (1e), carbon tetrabromide (0.20 g, 0.60 mmol), and triphenylphosphine (0.16 g, 0.60 mmol) in dichloromethane (1.0 ml) was stirred at 0° C. for 1 hour. Subsequently, to the reaction mixture were added successively ethyl 3-azetidinecarboxylate hydrochloride (0.12 g, 0.75 mmol) and N,N-diisopropylethylamine (0.26 ml, 1.5 mmol) at the same temperature with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, a saturated aqueous solution of sodium hydrogencarbonate (1.0 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was poured into water (20 ml) and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1 to 2:1) as the eluent to afford the title compound (0.21 g) in a yield of 84% as a white crystalline solid.

後処理

  1. stirringwith stirring
  2. stirringthe resulting mixture was stirred at room temperature for 2 hours
  3. stirringAfter stirring
  4. customto quench
  5. customthe reaction
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtration
  10. customthe filtrate was evaporated in vacuo

出典と根拠

ORDレコード
ord-5a815ec873a34b5fb1c09b3a7ae62f26
出典データセット
uspto-grants-2010_03
特許番号
US07687491B2

反応ノート

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