Potassium Carbonate → 4-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide

HRID 1446675

반응식

HRID 1446675 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])=[CH:11][CH:10]=2)O1.[Cl:32][C:33]1[CH:38]=[CH:37][N:36]2[C:39](I)=[CH:40][N:41]=[C:35]2[CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:32][C:33]1[CH:38]=[CH:37][N:36]2[C:39]([C:9]3[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=4)=[O:19])=[CH:13][CH:14]=3)=[CH:40][N:41]=[C:35]2[CH:34]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridineHCID 685460734-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide

생성물 1

HCID 685428324-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide수율 62.6%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

Suspend 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide (0.47 g, 1.15 mmol), 7-chloro-3-iodo-imidazo[1,2-a]pyridine (0.29 g, 1.05 mmol) and solid potassium carbonate (0.48 g, 3.45 mmol) in dioxane (4 mL) and water (2 mL). Deoxygenate the reaction contents with nitrogen for 10 minutes at room temperature. Add trans-dichlorobis(triphenylphosphine)palladium (II) (22 mg, 0.03 mmol) to the reaction. Fit a reflux condenser and heat the reaction to 105° C. over the weekend. Cool the reaction, dilute with dichloromethane and filter through Celite®. Concentrate the filtrate and then chromatograph on silica, using 0-3% methanol/ethyl acetate, to yield the product (301 mg, 57%). MS(ES), m/z 458 (M+1).

후처리

  1. customDeoxygenate
  2. customthe reaction contents with nitrogen for 10 minutes at room temperature
  3. temperatureheat
  4. customthe reaction to 105° C. over the weekend
  5. temperatureCool
  6. customthe reaction
  7. filtrationfilter through Celite®
  8. concentrationConcentrate the filtrate

출처 및 근거

ORD 기록
ord-66b40ce91cb54be4a6ddfcea1e681aaa
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666879B2

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