Benzyl Bromide → Ammonium Hydroxide

HRID 1585888ノート

反応式

HRID 1585888 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:39])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[N:16]=[CH:17][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:19]=3)=[CH:10][N:9]=2)[CH:7]=1.[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CC#N>[NH4+:6].[OH-:39].[CH2:40]([N:16]1[C:15]([CH2:14][C:11]2[CH:12]=[CH:13][C:8]([N:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]3=[O:39])=[N:9][CH:10]=2)=[CH:19][N:18]=[CH:17]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

参加物

5

反応物 2

HCID 7498Benzyl BromideHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

生成物 2

HCID 14923Ammonium Hydroxide収率 0.4%HCID 187797495'-(3-Benzyl-3H-imidazol-4-ylmethyl)-5-chloro-[1,2']bipyridinyl-2-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

A mixture of 5-chloro-5'-(1-triphenylmethyl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (0.10 g, 0.189 mmol) and benzyl bromide (0.036 g, 0.208 mmol) in CH3CN (1 mL) was heated at 50° C. for 18 h. The solvent was removed in vacuo and the residue was heated to reflux in MeOH (3 mL) for 1 h, then concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL). The organic layer was removed and the aqueous phase extracted further with CH2Cl2 (2×3 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with CH2Cl2 ; 4% MeOH; 0.4% NH4OH, to give the title compound:

後処理

  1. customThe solvent was removed in vacuo
  2. temperaturethe residue was heated
  3. temperatureto reflux in MeOH (3 mL) for 1 h
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL)
  6. customThe organic layer was removed
  7. extractionthe aqueous phase extracted further with CH2Cl2 (2×3 mL)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash column chromatography
  12. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-1fcb1bfd4a084dfe9069b45a64d41945
出典データセット
uspto-grants-1999_08
特許番号
US05939439

反応ノート

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