Potassium Carbonate → HCID 77230877, 화합물

HRID 402845

반응식

HRID 402845 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:14]=[O:15])=[CH:5][N:6]2[CH:11]([CH3:13])[CH3:12].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.Cl[Pd]Cl.[Fe]>[CH:16]1([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4]([CH:14]=[O:15])=[CH:5][N:6]3[CH:11]([CH3:13])[CH3:12])[CH2:18][CH2:17]1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 772308814-bromo-1-isopropyl-1H-indole-3-carbaldehyde

생성물 1

HCID 77230877HCID 77230877, 화합물수율 18.5%

시약·촉매·용매 3

HCID 178454869HCID 178454869, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
140 °C

실험 절차

To a solution of 4-romo-1-(propan-2-yl)-1H-indole-3-carboxaldehyde (120 mg, 0.451 mmol) (from Example 9-1, Step 1) and cyclopropylboronic acid (77 mg, 0.902 mmol) in dioxane (2 mL) and water (0.5 mL) in a 5 mL microwave reaction vial was added potassium carbonate (187 mg, 1.35 mmol) and dichloro[1,1′-bis(di-t-butylphosphino)ferrocene]palladium (II) (29 mg, 0.045 mmol). The reaction was placed under nitrogen, sealed and heated in a microwave reactor at 140° C. for 25 minutes. The solvent was removed in vacuo and the residue was partitioned with ethyl acetate and aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes) to give the title intermediate (19 mg).

후처리

  1. customsealed
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned with ethyl acetate and aqueous sodium bicarbonate
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-c464cef29b1846db90279fe2d76f9849
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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