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Pyridine → HCID 22319520、化合物

HRID 497667
ノート
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反応式

HRID 497667 の反応式
N1C=CC=CC=1.[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([NH:25][C:26](=[O:30])[CH2:27][CH2:28][CH3:29])=[N:13][N:14]2[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][CH:9]=1.[Br:31]Br>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:31][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:8]=1[Br:7])[N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:22])[CH3:23])[N:13]=[C:12]2[NH:25][C:26](=[O:30])[CH2:27][CH2:28][CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049PyridineHCID 24408BromineHCID 22319559N-[6-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide

生成物 1

HCID 22319520HCID 22319520、化合物

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

3.3 cm3 of pyridine are added to 4 g of N-[6-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously in Example 51, in 80 cm3 of chloroform, followed by dropwise addition of 2 cm3 of bromine, and the mixture is then left stirring for 18 hours. The reaction medium is diluted with 100 cm3 of methylene chloride and the organic phase is washed with 2×100 cm3 of 10% sodium thiosulphate solution and then with 75 cm3 of saturated sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50° C.). The crude product is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.), then dried (90 Pa; 45° C.) to give 4.24 g of N-[5,6-dibromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide in the form of a yellow solid melting at 134° C.

後処理

  1. waitthe mixture is then left
  2. washthe organic phase is washed with 2×100 cm3 of 10% sodium thiosulphate solution
  3. customThe organic phase is separated out
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  7. customThe crude product is purified by chromatography under an argon pressure of 50 kPa
  8. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  9. additionThe fractions containing the expected product
  10. customevaporated under reduced pressure (2 kPa; 50° C.)
  11. customdried (90 Pa; 45° C.)

出典と根拠

ORDレコード
ord-1d3d2df718184c5c9d4d5fb54360f7a2
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949579B2

反応ノート

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