Potassium Acetate → 5-(2-(2-methylpyrid-3-yl)-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole

HRID 628096

반응식

HRID 628096 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][CH2:8][C:9]3[CH:15]=[C:14]([C:16]4[N:20]([C:21]5[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=5[F:28])[N:19]=[CH:18][N:17]=4)[S:13][C:10]=3[C:11]=2[N:12]=1.C([O-])(=O)C.[K+].[CH3:34][C:35]1[C:40](B(O)O)=[CH:39][CH:38]=[CH:37][N:36]=1>C(#N)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:34][C:35]1[C:40]([C:2]2[CH:3]=[CH:4][C:5]3[O:6][CH2:7][CH2:8][C:9]4[CH:15]=[C:14]([C:16]5[N:20]([C:21]6[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=6[F:28])[N:19]=[CH:18][N:17]=5)[S:13][C:10]=4[C:11]=3[N:12]=2)=[CH:39][CH:38]=[CH:37][N:36]=1

참가 물질

7

반응물 3

HCID 517044Potassium AcetateHCID 201116472-Methylpyridine-3-boronic acidHCID 579003099-Chloro-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene

생성물 1

HCID 579003825-(2-(2-methylpyrid-3-yl)-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole수율 70%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

5-(2-(Chloro)-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole (50 mg, 0.1 mmol) was dissolved in 1 ml acetonitrile and 1 ml water, with potassium acetate (39.9 mg, 0.406 mmol). The solution was degassed by bubbling with nitrogen for 5 min. 2-Methylpyridin-3-ylboronic acid (21.4 mg, 0.156 mmol) was added, then tetrakis(triphenylphosphine)palladium(0) (19 mg, 0.016 mmol). The reaction was microwaved at 300 watts, 140° C. for 20 minutes, cooled to room temperature, and extracted with ethyl acetate. The combined organics were concentrated and purified by reverse phase HPLC to give 474 (70% yield). MS: (ESI+)=474.0

후처리

  1. customThe solution was degassed
  2. customby bubbling with nitrogen for 5 min
  3. customThe reaction was microwaved at 300 watts, 140° C. for 20 minutes
  4. extractionextracted with ethyl acetate
  5. concentrationThe combined organics were concentrated
  6. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-b80972940e0e4740ab7562a9ef8f4353
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309265B2

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