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

HRID 923276노트

반응식

HRID 923276 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4dbe04ba765245c0b8f02b1b0de51b16
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278969B2

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