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Oxygen → 1-[3-(Pentafluorosulfanyl)-5-pyrrolidin-1-ylphenyl]ethanone

HRID 1258536
ノート
印刷プレビュー

反応式

HRID 1258536 の反応式
Br[C:2]1[CH:7]=[C:6]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:14]([O:18]C)(OC)[CH3:15])[CH:3]=1.O=O.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.CC(C)([O-])C.[Na+]>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(=O)OCC>[F:13][S:8]([F:10])([F:11])([F:12])([F:9])[C:6]1[CH:5]=[C:4]([C:14](=[O:18])[CH3:15])[CH:3]=[C:2]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 977OxygenHCID 31268PyrrolidineHCID 23676156Sodium t-butoxideHCID 581374181-Bromo-3-(1,1-dimethoxyethyl)-5-(pentafluorosulfanyl)benzene

生成物 1

HCID 581374371-[3-(Pentafluorosulfanyl)-5-pyrrolidin-1-ylphenyl]ethanone

試薬・触媒・溶媒 5

HCID 962Water触媒
HCID 167845palladium(II) acetate触媒
HCID 634876Binap, (A+-)-触媒
HCID 80711,2-Dimethoxyethane溶媒2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

1-Bromo-3-(1,1-dimethoxyethyl)-5-(pentafluorosulfanyl)benzene (200 mg) was initially charged at RT in DME (30 ml) under argon. Two drops of water were added to the DME. A strong argon stream was used to displace the oxygen from the solution for 45 min. Then pyrrolidine (45 μl) was added dropwise through a septum, followed by (+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (5 mg), sodium tert-butoxide (73 mg) and palladium(II) acetate (1.2 mg). The reaction mixture was heated to 85° C. for 3 h. Then EA was added to the reaction mixture and, after removing the EA phase, the aqueous phase was extracted three times with EA. The combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in ACN/water and adjusted to pH 2 with 1N hydrochloric acid. After standing for 30 min, the mixture was concentrated and the residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile, admixed with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 55 mg of the desired compound were obtained.

後処理

  1. customfor 45 min
  2. customafter removing the EA phase
  3. extractionthe aqueous phase was extracted three times with EA
  4. dry with materialThe combined EA phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ACN/water
  8. concentrationthe mixture was concentrated
  9. customthe residue was purified by means of preparative HPLC
  10. extractionextracted three times with ethyl acetate
  11. dry with materialThe combined extracts were dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-9b7c41b31b20490cade1bc61205da32d
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466169B2

反応ノート

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