furo[2,3-b]pyridine-5-carbaldehyde → HCID 68415383、化合物

HRID 220269ノート

反応式

HRID 220269 の反応式
[Cl-].[CH3:2][NH:3][C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[Li]CCCC.[O:31]1[C:35]2=[N:36][CH:37]=[C:38]([CH:40]=O)[CH:39]=[C:34]2[CH:33]=[CH:32]1>C1COCC1>[O:31]1[C:35]2=[N:36][CH:37]=[C:38]([CH:40]=[CH:6][C:4]([NH:3][CH3:2])=[O:5])[CH:39]=[C:34]2[CH:33]=[CH:32]1

参加物

5

反応物 3

HCID 10749327furo[2,3-b]pyridine-5-carbaldehydeHCID 85777853HCID 85777853、化合物HCID 178418339Butyllithium

生成物 1

HCID 68415383HCID 68415383、化合物収率 95.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 0.25 g of methylcarbamoylmethyl-triphenyl-phosphonium chloride (J. Med. Chem. 2003, 46, 399) in 1 ml of THF was added 0.88 ml of n-BuLi (1.6M) at −60° C. After stirring for 1 h at −60° C. a solution of 0.1 g of furo[2,3-b]pyridine-5-carbaldehyde in 1 ml of THF was added and the resulting reaction mixture was stirred for 5 h reaching slowly rt. The reaction mixture was poured over ice. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by CC using EtOAc as eluant yielded 0.13 g of 3-furo[2,3-b]pyridin-5-yl-N-methyl-acrylamide as a mixture of E/Z isomers.

後処理

  1. additionwas added
  2. customthe resulting reaction mixture
  3. customreaching slowly rt
  4. additionThe reaction mixture was poured over ice
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by CC

出典と根拠

ORDレコード
ord-3f5be8ed752d43c9a7e44daed6b1989c
出典データセット
uspto-grants-2012_06
特許番号
US08202885B2

反応ノート

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