Sodium Bicarbonate → HCID 68473716、化合物

HRID 387672ノート

反応式

HRID 387672 の反応式
Br[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[C:9]([C:10]1[CH:5]=[C:4]([C:2]2[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]3[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=3[CH:11]=2)[CH:3]=[CH:2][CH:11]=1)#[N:8]

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 68473018HCID 68473018、化合物

生成物 1

HCID 68473716HCID 68473716、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

Added to a solution of 0.3 g of methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate in 9.4 cm3 of dioxane and 1.8 cm3 of water, at a temperature close to 20° C., are 147 mg of sodium bicarbonate. The reaction medium is then degassed under an argon atmosphere, then 111 mg of 3-cyanophenylboronic acid and 72 mg of tetrakis(triphenylphosphine)palladium are added. The mixture is heated at 150° C. in a microwave oven for 4 minutes, cooled to a temperature close to 20° C. and filtered. The filtrate is dried over anhydrous magnesium sulfate then filtered; added to the filtrate is 1 g of silica and the absorbed residue is purified by flash chromatography over silica (column: 15 g; spherical silica of BP-SUP type, particle size: 20-40 μm, eluent: 80% heptane/20% ethyl acetate then 60% heptane/40% ethyl acetate). After concentrating the fractions under reduced pressure, 103 mg of methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are obtained in the form of an orange oil.

後処理

  1. customclose to 20° C.
  2. customThe reaction medium is then degassed under an argon atmosphere
  3. addition111 mg of 3-cyanophenylboronic acid and 72 mg of tetrakis(triphenylphosphine)palladium are added
  4. temperaturecooled to a temperature
  5. customclose to 20° C.
  6. filtrationfiltered
  7. dry with materialThe filtrate is dried over anhydrous magnesium sulfate
  8. filtrationthen filtered
  9. additionadded to the filtrate
  10. customthe absorbed residue is purified by flash chromatography over silica (column
  11. concentrationAfter concentrating the fractions under reduced pressure, 103 mg of methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate
  12. customare obtained in the form of an orange oil

出典と根拠

ORDレコード
ord-f1a425bffd274329a8061377846cb5f2
出典データセット
uspto-grants-2013_02
特許番号
US08372864B2

反応ノート

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