Potassium Carbonate → 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]acetamide

HRID 1054734

반응식

HRID 1054734 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.[C:19](=O)([O-])[O-:20].[K+].[K+].Br[C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32]([NH2:34])=[O:33])=[CH:28][CH:27]=1>O1CCOCC1.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:20])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32]([NH2:34])=[O:33])=[CH:28][CH:27]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 3028642-(4-Bromophenoxy)acetamideHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

생성물 1

HCID 866987342-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]acetamide수율 76%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (260 mg, 1.00 mmol) and N,N-dimethylformiminium chloride (250 mg, 2.00 mmol) in dry 1,4-dioxane (5 mL) and DMF (1 mL) was sealed in a reaction vessel and stirred at room temperature for 10 minutes to give a white slurry. To the slurry was added 2 M aqueous potassium carbonate (2.5 mL, 5 mmol), 2-(4-bromophenoxy)acetamide (240 mg, 1.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg). The sealed vial was degassed with nitrogen and heated to 90° C. for 30 minutes. The reaction was quenched with water (20 mL), and extracted with EtOAc (3×20 mL). The combined organic layers were dried and concentrated in vacuo to give 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]acetamide (250 mg, 55% yield) as a yellow solid.

후처리

  1. customwas sealed in a reaction vessel
  2. customto give a white slurry
  3. customThe sealed vial was degassed with nitrogen
  4. temperatureheated to 90° C. for 30 minutes
  5. customThe reaction was quenched with water (20 mL)
  6. extractionextracted with EtOAc (3×20 mL)
  7. customThe combined organic layers were dried
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1449158dba894e66bf16fc9c42bb422d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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