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Hydrochloric Acid → [4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-hydroxy-2-(2,4,6-trifluoro-phenyl)naphthalen-1-yl]-methanone

HRID 1513899
ノート
印刷プレビュー

反応式

HRID 1513899 の反応式
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:29]C)=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[C:31]3[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=3[F:39])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl.CO>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[C:31]3[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=3[F:39])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57552563[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-methoxy-2-(2,4,6-trifluoro phenyl)-naphthalen-1-yl]-methanone

生成物 1

HCID 67004267[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-hydroxy-2-(2,4,6-trifluoro-phenyl)naphthalen-1-yl]-methanone収率 57%

試薬・触媒・溶媒

2
HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Dissolve [4-(2-azepan-1-yl-ethoxy)-phenyl]-[6-methoxy-2-(2,4,6-trifluoro-phenyl)-naphthalen-1-yl]-methanone (634 mg, 1.2 mmol) in dichloromethane (10 mL). Cool to 0° C., add HCl (2M in ether, 1.2 mL, 2.4 mmol) and stir at room temperature for 15 minutes. Concentrate in vacuo. Redissolve the salt in dichloromethane (10 mL) and cool to 0° C. Add boron tribromide (949 mg, 3.6 mmol) dropwise and bring to room temperature. Stir reaction for 1.5 hour and pour reaction mixture onto ice, saturated sodium bicarbonate (20 mL) and methanol (20 mL). Extract with dichloromethane, combine extracts and wash with water and saturated sodium bicarbonate. Dry with sodium sulfate, filter, and concentrate in vacuo. Purify by silica gel chromatography using a 1-3% gradient of methanol in dichloromethane to yield 350 mg (57%) of the title compound: mass spectrum (ion spray) m/z=520 (M+H).

後処理

  1. concentrationConcentrate in vacuo
  2. dissolutionRedissolve the salt in dichloromethane (10 mL)
  3. temperaturecool to 0° C
  4. custombring to room temperature
  5. stirringStir
  6. customreaction for 1.5 hour
  7. additionpour
  8. extractionExtract with dichloromethane
  9. washwash with water and saturated sodium bicarbonate
  10. dry with materialDry with sodium sulfate
  11. filtrationfilter
  12. concentrationconcentrate in vacuo
  13. customPurify by silica gel chromatography

出典と根拠

ORDレコード
ord-564f426970554b868eace84828770092
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217032B2

反応ノート

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