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 335824ノート

反応式

HRID 335824 の反応式
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

参加物

7

反応物 3

HCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acidHCID 58466199HCID 58466199、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-bb0842e56e794a4b8fb470ac6b77be19
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

読み込み中…