Ammonia → 4-bromo-2-methyl-2,3-dihydro-1H-indole

HRID 2278597ノート

反応式

HRID 2278597 の反応式
C([BH3-])#N.[Na+].[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([CH3:15])[NH:10]2.N>C(O)(=O)C>[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH:9]([CH3:15])[NH:10]2

参加物

5

反応物 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 218145664-Bromo-2-methyl-1H-indole

生成物 1

HCID 107272374-bromo-2-methyl-2,3-dihydro-1H-indole

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
14 °C

実験手順

7.99 g of sodium cyanoborohydride are gradually added to a solution of 8.90 g of 4-bromo-2-methylindole (which can be prepared according to patent US2010/160647 A1, 2010) in 310 ml of acetic acid under argon cooled to a temperature of about 14° C. The reaction mixture is stirred at a temperature of about 14° C. for 15 minutes, and it is then allowed to warm up to ambient temperature. After 2 hours, the reaction mixture is poured into an Erlenmeyer flask containing ice-cold water (200 ml) and then the pH is brought to 9 with an aqueous ammonia solution. The reaction medium is extracted with dichloromethane (2×200 ml) and then the organic phases are combined, washed with water, dried over magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. After purification of the residue by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (90/10), 5.92 g of 4-bromo-2-methylindoline are obtained, the characteristics of which are the following:

後処理

  1. temperatureto warm up to ambient temperature
  2. waitAfter 2 hours
  3. additionthe reaction mixture is poured into an Erlenmeyer flask
  4. extractionThe reaction medium is extracted with dichloromethane (2×200 ml)
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customAfter purification of the residue
  10. washby silica column chromatography, elution
  11. additionbeing carried out with a mixture of heptane and ethyl acetate (90/10), 5.92 g of 4-bromo-2-methylindoline
  12. customare obtained

出典と根拠

ORDレコード
ord-2fe060e40a43404c9465eb5e114f0334
出典データセット
uspto-grants-2015_09
特許番号
US09133168B2

反応ノート

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