Bromine → Eudistomin O

HRID 1168715ノート

反応式

HRID 1168715 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:13][C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:5]=2[CH:6]=1.[Br:14]Br>O1CCCC1>[Br:14][C:2]1[CH:3]=[C:4]2[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][C:12]=3[NH:13]2)=[CH:6][CH:1]=1

参加物

4

反応物 2

HCID 24408BromineHCID 64961Beta-Carboline

生成物 1

HCID 145928Eudistomin O収率 65.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of norharmane (600 mg, 3.57 mmol) in tetrahydrofuran (THF; 50 ml) was treated with bromine (0.40 ml, 7.80 mmol) at RT while stirring. After stirring for 18 h at RT, the reaction was concentrated under reduced pressure and the resulting residue was sonicated in 10% aqueous Na2CO3 (100 ml). The product was filtered and washed with water to give 905 mg of crude product. The crude product was crystallized from xylenes to provide in two crops 580 mg of 7-bromo-β-carboline.

後処理

  1. stirringAfter stirring for 18 h at RT
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customthe resulting residue was sonicated in 10% aqueous Na2CO3 (100 ml)
  4. filtrationThe product was filtered
  5. washwashed with water
  6. customto give 905 mg of crude product
  7. customThe crude product was crystallized from xylenes

出典と根拠

ORDレコード
ord-4d0ad88717a943eeb5254d57152975b3
出典データセット
uspto-grants-2003_09
特許番号
US06627637B2

反応ノート

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