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

HRID 2060363

반응식

HRID 2060363 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-303eae82c25440e5b034011d6793065f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278322B2

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