Triethylamine → 7-Bromo-6-methoxy-1(2H)-isoquinolinone

HRID 2060363

反応式

HRID 2060363 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/C(O)=O)=[CH:4][C:3]=1[O:13][CH3:14].C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:8]=[CH:9][NH:17][C:20]2=[O:29])=[CH:4][C:3]=1[O:13][CH3:14]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 580051274-Bromo-3-methoxycinnamic acid

生成物 1

HCID 580051257-Bromo-6-methoxy-1(2H)-isoquinolinone収率 59.9%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

A portion of the product from Step 1 [(2E)-3-(4-bromo-3-methoxyphenyl)acrylic acid](12.5 g, 48.6 mmol) was azeotroped with benzene and suspended in benzene (94 mL). Triethylamine (9.49 mL, 68.1 mmol) and diphenylphosphoryl azide (10.48 mL, 48.6 mmol) were added and the reaction mixture stirred at RT for 1 h. The mixture was filtered through a pad of silica and eluted with ˜1 L of toluene, the volatiles evaporated, the residue resuspended in diphenylmethane (94 mL) and the mixture heated to reflux for three hours (internal temperature 250° C.). The reaction mixture was allowed to cool to RT, stirred overnight, filtered and the solid washed with hexanes (100 mL) to give tan solid (7.4 g). LRMS ESI+ (M+H)+ 254.1.

後処理

  1. filtrationThe mixture was filtered through a pad of silica
  2. washeluted with ˜1 L of toluene
  3. customthe volatiles evaporated
  4. temperaturethe mixture heated
  5. temperatureto reflux for three hours (internal temperature 250° C.)
  6. temperatureto cool to RT
  7. stirringstirred overnight
  8. filtrationfiltered
  9. washthe solid washed with hexanes (100 mL)

出典と根拠

ORDレコード
ord-303eae82c25440e5b034011d6793065f
出典データセット
uspto-grants-2012_10
特許番号
US08278322B2

関連ノート

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