Potassium Acetate → 2-fluoro-7-(2-fluoropyridin-3-yl)-3-(trimethylsilyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

HRID 335824노트

반응식

HRID 335824 반응식
Br[C:2]1[CH:3]=[C:4]2[C:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[C:9](=[N:10][C:11]([F:25])=[C:12]([Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:13]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[F:26][C:27]1[C:32](B(O)O)=[CH:31][CH:30]=[CH:29][N:28]=1.C([O-])(=O)C.[K+]>C(O)C.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[F:25][C:11]1[N:10]=[C:9]2[O:8][C:5]3[C:4]([C:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:14]2=[CH:13][C:12]=1[Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:3][C:2]([C:32]1[C:27]([F:26])=[N:28][CH:29]=[CH:30][CH:31]=1)=[CH:7][CH:6]=3

참가 물질

7

반응물 3

HCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acidHCID 58466199HCID 58466199, 화합물

생성물 1

HCID 673835332-fluoro-7-(2-fluoropyridin-3-yl)-3-(trimethylsilyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

시약·촉매·용매 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 702Ethanol용매HCID 962Water용매

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온도
80 °C

실험 절차

7-Bromo-2-fluoro-3-(trimethylsilyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.137 g, 0.324 mmol), bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(ii) (0.011 g, 0.016 mmol), 2-fluoropyridin-3-ylboronic acid (0.055 g, 0.389 mmol), and potassium acetate (0.127 g, 1.298 mmol) were suspended in a mixture of ethanol (30 mL) and water (5 mL) and heated to 80° C. After 20 minutes the solution was cooled to rt and concentrated under reduced pressure to ˜10 mL. This solution was then diluted with water (100 mL) and EtOAc (100 mL). The phases were mixed and separated and the organics were dried with magnesium sulfate before filtered and evaporated to dryness under reduced pressure. Purification using silica chromatography (0-10% methanol in DCM gradient followed by a second column using dichloromethane to EtOAc gradient) gave the desired 2-fluoro-7-(2-fluoropyridin-3-yl)-3-(trimethylsilyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine

후처리

  1. temperatureAfter 20 minutes the solution was cooled to rt
  2. concentrationconcentrated under reduced pressure to ˜10 mL
  3. additionThis solution was then diluted with water (100 mL) and EtOAc (100 mL)
  4. additionThe phases were mixed
  5. customseparated
  6. dry with materialthe organics were dried with magnesium sulfate
  7. filtrationbefore filtered
  8. customevaporated to dryness under reduced pressure
  9. customPurification

출처 및 근거

ORD 기록
ord-bb0842e56e794a4b8fb470ac6b77be19
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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