Toluene → propane-1-sulfonic acid {3-[1-(2,6-dichloro-benzoyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide

HRID 60104

반응식

HRID 60104 반응식
[F:1][C:2]1[C:7]([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([B:19]4[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]4)[CH:17]=3)[NH:12][CH:11]=2)=[O:9])=[C:6]([F:28])[CH:5]=[CH:4][C:3]=1[NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31].C1(C)C=CC=CC=1.C(NC(C)C)(C)C.[Cl:50][C:51]1[CH:59]=[CH:58][CH:57]=[C:56]([Cl:60])[C:52]=1[C:53](Cl)=[O:54]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:50][C:51]1[CH:59]=[CH:58][CH:57]=[C:56]([Cl:60])[C:52]=1[C:53]([N:12]1[C:13]2=[N:14][CH:15]=[C:16]([B:19]3[O:20][C:21]([CH3:26])([CH3:27])[C:22]([CH3:24])([CH3:25])[O:23]3)[CH:17]=[C:18]2[C:10]([C:8]([C:7]2[C:2]([F:1])=[C:3]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:31])=[O:32])[CH:4]=[CH:5][C:6]=2[F:28])=[O:9])=[CH:11]1)=[O:54]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 7912DiisopropylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 58368878propane-1-sulfonic acid (2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl)-amide

생성물 1

HCID 58368752propane-1-sulfonic acid {3-[1-(2,6-dichloro-benzoyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

Propane-1-sulfonic acid {2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide (30, 2.1 g, 4.16 mmol), 21 mL of toluene, diisopropylamine (1.5 mL, 8.31 mmol), 4-dimethylaminopyridine (101 mg, 0.83 mmol) and 2,6-dichloro-benzoyl chloride (10, 0.7 mL, 4.78 mmol) are combined in a reaction flask under nitrogen. The reaction is stirred at room temperature for 17 hours, then diluted with 100 mL of ethyl acetate and extracted. The organic layer is washed sequentially with 40 mL of saturated aqueous sodium bicarbonate, 40 mL of water, and 40 mL of brine, then dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum and the resulting material is triturated with diethyl ether to provide the desired compound.

후처리

  1. extractionextracted
  2. washThe organic layer is washed sequentially with 40 mL of saturated aqueous sodium bicarbonate, 40 mL of water, and 40 mL of brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with a gradient of ethyl acetate and hexane
  8. concentrationconcentrated under vacuum
  9. customthe resulting material is triturated with diethyl ether

출처 및 근거

ORD 기록
ord-6bbb0535581a4d15b116704b9443d3c9
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440969B2

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