Cesium carbonate → 2-bromo-6-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)benzaldehyde

HRID 1644211노트

반응식

HRID 1644211 반응식
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]=[O:5].[C:11]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[NH:20][N:19]=[CH:18]2)([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1>[Cu]I.O1CCOCC1>[Br:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([N:20]2[N:19]=[CH:18][C:17]3[C:22](=[CH:23][CH:24]=[C:15]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:16]=3)[C:21]2=[O:25])[C:3]=1[CH:4]=[O:5]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 126486412,6-DibromobenzaldehydeHCID 576339336-(tert-butyl)phthalazin-1(2H)-one

생성물 1

HCID 580161852-bromo-6-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)benzaldehyde수율 69.1%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

5.90 g (22.4 mmol) of 2,6-dibromobenzaldehyde, 1.80 g (8.90 mmol) of 6-tert-butyl-2H-phthalazin-1-one, 6.02 g (18.5 mmol) of cesium carbonate, 179 mg (0.940 mmol) of copper(I) iodide, and 428 mg (1.87 mmol) of 4,7-dimethoxy-1,10-phenanthroline were weighed into a 100 mL reaction flask fitted with a stir bar and septum cap. Added 50 mL of anhydrous dioxane. Purged the reaction mixture with nitrogen for 15 min. Stirred at 100° for 18 h. Partitioned the reaction mixture between 200 mL of 10% MeOH/CH2Cl2 and 200 mL of water. Separated phases and extracted the aqueous phase with 2×100 mL of 10% MeOH/CH2Cl2. The combined organic extracts were washed with 200 mL of brine, dried over Na2SO4, and the solvent was removed on rotavap. Purified the crude by flash chromatography on silica gel to obtain 2.37 g of the title compound as an off-white solid. MS (ESI) doublet 385, 387 (M+H)+.

후처리

  1. customfitted with a stir bar
  2. customseptum cap
  3. customPurged the reaction mixture with nitrogen for 15 min
  4. customPartitioned the reaction mixture between 200 mL of 10% MeOH/CH2Cl2 and 200 mL of water
  5. extractionSeparated phases and extracted the aqueous phase with 2×100 mL of 10% MeOH/CH2Cl2
  6. washThe combined organic extracts were washed with 200 mL of brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed on rotavap
  9. customPurified the crude by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-06397d36b03640b9bc2d8b9d7efb6adb
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124604B2

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