Potassium Carbonate → HCID 118021393, 화합물

HRID 531234노트

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HRID 531234 반응식
Br[C:2]1[C:3]([CH2:10][N:11]2[C@@H:15]([CH3:16])[C@@H:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=3)[O:13][C:12]2=[O:28])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[Cl:29][C:30]1[CH:31]=[C:32](B(O)O)[C:33]([O:36][CH3:37])=[N:34][CH:35]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[Cl:29][C:30]1[CH:31]=[C:32]([C:2]2[C:3]([CH2:10][N:11]3[C@@H:15]([CH3:16])[C@@H:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=4)[O:13][C:12]3=[O:28])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=2)[C:33]([O:36][CH3:37])=[N:34][CH:35]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 44754881(5-Chloro-2-methoxypyridin-3-yl)boronic acidHCID 90009127(4S,5R)-3-{[5-Bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazolidin-2-one2회

생성물 1

HCID 118021393HCID 118021393, 화합물

시약·촉매·용매 2

HCID 178454861HCID 178454861, 화합물촉매HCID 6342Acetonitrile용매

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온도
85 °C

실험 절차

(4S,5R)-3-{[5-Bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazolidin-2-one (INTERMEDIATE 9, 345 mg, 0.721 mmol), 5-chloro-2-methoxypyridin-3-ylboronic acid (203 mg, 1.082 mmol) and K2CO3 (299 mg, 2.164 mmol) were added to a round bottom flask, which was then evacuated and charged with nitrogen 3 times. THF (4 mL) and water (0.4 mL) were then added. After evacuating and charging again with nitrogen, 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (47.0 mg, 0.072 mmol) was added and the reaction heated for 60 minutes at 85° C. LCMS showed complete conversion to product. The reaction was diluted with 5 mL acetonitrile and filtered through a 1 g C18 cartridge, eluting with 15 mL acetonitrile until the filtrate was colorless. The filtrate was then concentrated. Silica gel chromatography using a 0-30% ethyl acetate/hexanes linear gradient followed by an isocratic hold of 30% ethyl acetate/hexanes gave the title compound as a colorless oil. LCMS (M+H)+: 541.2.

후처리

  1. customwhich was then evacuated
  2. additioncharged with nitrogen 3 times
  3. additionTHF (4 mL) and water (0.4 mL) were then added
  4. customAfter evacuating
  5. additionwas added
  6. filtrationfiltered through a 1 g C18 cartridge
  7. washeluting with 15 mL acetonitrile until the filtrate
  8. concentrationThe filtrate was then concentrated

출처 및 근거

ORD 기록
ord-41bbc5ef80964285b97a197dfa3f96c5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353101B2

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