Carbon Dioxide → 5-methoxy-1H-indole-7-carboxylic acid

HRID 661339ノート

反応式

HRID 661339 の反応式
Br[C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[Li]CCCC.[C:18](=[O:20])=[O:19]>C1COCC1.CCCCCC>[CH3:12][O:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([C:18]([OH:20])=[O:19])[CH:3]=1)[NH:9][CH:8]=[CH:7]2

参加物

6

反応物 3

HCID 280Carbon DioxideHCID 198041607-Bromo-5-methoxy-1H-indoleHCID 178418339Butyllithium

生成物 1

HCID 597466045-methoxy-1H-indole-7-carboxylic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A solution of 7-Bromo-5-methoxy-1H-indole (described in WO 2002028861) in THF was treated with 2 eq. of a solution of n-BuLi in n-hexane (1.6M) at 5° and after 30 min at this temperature was cooled to −75°. Dry ice (excess) was added and after 15 mins the mixture was quenched with H2O and washed with EtOAc. After acidification of the aqueous layer and extraction into CH2Cl2, evaporation gave the desired product.

後処理

  1. temperaturewas cooled to −75°
  2. customwas quenched with H2O
  3. washwashed with EtOAc
  4. extractionAfter acidification of the aqueous layer and extraction
  5. custominto CH2Cl2, evaporation

出典と根拠

ORDレコード
ord-5b555b3220984de8a2f53c54beac1c55
出典データセット
uspto-grants-2011_12
特許番号
US08084609B2

反応ノート

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