Water → N-{2-[2-Methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide

HRID 1262334노트

반응식

HRID 1262334 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[N:29]2[C:24]([CH:25]=[N:26][C:27]([S:30][CH3:31])=[N:28]2)=[C:23]([O:32][CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:22]=1.CC1(C)C(C)(C)OB([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[NH:55][S:56]([CH3:59])(=[O:58])=[O:57])O1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+].O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:31][S:30][C:27]1[N:26]=[CH:25][C:24]2=[C:23]([O:32][CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:22]=[C:21]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[NH:55][S:56]([CH3:59])(=[O:58])=[O:57])[N:29]2[N:28]=1

참가 물질

8

반응물 6

HCID 962WaterHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 43565252-(Methanesulfonylamino)phenylboronic acid pinacol esterHCID 667122877-Bromo-2-methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazine

생성물 1

HCID 66712259N-{2-[2-Methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide수율 78%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

Into a 30 mL vial, Palladium Acetate (0.043 g, 0.19 mmol) and Triphenylphosphine (0.14 g, 0.54 mmol) were added. The mixture was purged under an atmosphere of Nitrogen for 10 minutes. 1,4-Dioxane (14.6 mL) was added and stirred for 10 minutes at room temperature. 7-Bromo-2-methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazine (0.750 g, 1.92 mmol), N-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide (1.14 g, 3.84 mmol), N,N-Dimethylformamide (29 mL, 380 mmol), and 1.50 M of Sodium carbonate in Water (11.5 mL, 17.3 mmol) were added. The reaction was heated at 90° C. for 3 hours. The reaction was partitioned with water and EtOAc. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolated via column chromatography with DCM and Methanol as eluant (0 to 5% MeOH). The collected fractions afforded a solid. The solid was triturated with Et2O and filtered to give N-{2-[2-Methylsulfanyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide as a yellow solid (0.72 g, 78%).

후처리

  1. customThe mixture was purged under an atmosphere of Nitrogen for 10 minutes
  2. addition1,4-Dioxane (14.6 mL) was added
  3. temperatureThe reaction was heated at 90° C. for 3 hours
  4. customThe reaction was partitioned with water and EtOAc
  5. customThe organic was separated
  6. washwashed with Brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe solid was filtered
  9. washwashed with EtOAc
  10. customThe solvent was removed under vacuum
  11. customThe product was isolated via column chromatography with DCM and Methanol as eluant (0 to 5% MeOH)
  12. customThe collected fractions afforded a solid
  13. customThe solid was triturated with Et2O
  14. filtrationfiltered

출처 및 근거

ORD 기록
ord-640ff7fae49d4e9e9822ba060e935c65
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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