Acetic Acid → 2-Bromo-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 1888471ノート

反応式

HRID 1888471 の反応式
[BH4-].[Na+].Br.[Br:4][C:5]1[S:13][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1.[C:14](O)(=O)[CH3:15]>O1CCCC1>[Br:4][C:5]1[S:13][C:8]2[CH2:9][N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][C:7]=2[CH:6]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 670276802-bromo-4H,5H,6H,7H-thieno(2,3-c)pyridine hydrobromide

生成物 1

HCID 582664752-Bromo-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Sodium borohydride (146 mg, 3.85 mmol) was added to cooled (0° C.) a suspension of 2-bromo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide (230 mg, 0.77 mmol) in acetic acid (1.5 mL) and tetrahydrofuran (2.8 mL). On complete addition the mixture was heated to 60° C. for 3 h. The mixture was allowed to cool to ambient temperature then partitioned between ethyl acetate and water. The pH of the aqueous phase was adjusted to 10 by the addition of 3N sodium hydroxide solution and the layers separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to give the title compound as a yellow oil (181 mg, 96%). 1H NMR (DMSO-D6, 300 MHz): 6.93 (s, 1H), 3.50-3.47 (m, 2H), 3.66-2.46 (m, 6H), 1.05 (t, J=7.2 Hz, 3H). LCMS (Method B): RT=1.79 min, M+H+=246/248.

後処理

  1. additionOn complete addition the mixture
  2. temperaturewas heated to 60° C. for 3 h
  3. temperatureto cool to ambient temperature
  4. customthen partitioned between ethyl acetate and water
  5. additionThe pH of the aqueous phase was adjusted to 10 by the addition of 3N sodium hydroxide solution
  6. customthe layers separated
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

出典と根拠

ORDレコード
ord-18c40b3c753b439c8187cef7429f26d2
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

読み込み中…