N,N,N',N'-Tetramethylethylenediamine → 5-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 76895ノート

反応式

HRID 76895 の反応式
[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[C:9]([CH2:10][CH2:11][CH2:12]Cl)=[CH:8][N:7]=[CH:6]1.CN(CCN(C)C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH:4]1[N:5]2[CH:6]=[N:7][CH:8]=[C:9]2[CH2:10][CH2:11][CH2:12]1

参加物

5

反応物 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2724682Lithium diisopropylamideHCID 588270851-(2-Bromobenzyl)-5-(3-chloropropyl)-1H-imidazole

生成物 1

HCID 588271225-(2-Bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a slurry of 1-(2-bromobenzyl)-5-(3-chloropropyl)-1H-imidazole (0.662 g, 2.12 mmol) and TMEDA (0.683 mL, 4.55 mmol) in THF (10 mL) at −78° C. is added LDA (1.8 M in heptane/THF/ethylbenzene, 2.5 mL, 4.5 mmol) and the yellow clear solution is stirred at −78° C. After 3.5 hr, the reaction is quenched by saturated aqueous NH4Cl, and the mixture is partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer is washed with brine, dried and concentrated to give an oil, which is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 277 (M+H).

後処理

  1. customthe reaction is quenched by saturated aqueous NH4Cl
  2. customthe mixture is partitioned between EtOAc and saturated aqueous NaHCO3
  3. washThe organic layer is washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil, which
  7. washeluting with MeOH

出典と根拠

ORDレコード
ord-7322af3dfd524bfab924f8ebf454cd61
出典データセット
uspto-grants-2014_09
特許番号
US08835646B2

反応ノート

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