N,N,N',N'-Tetramethylethylenediamine → [2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-pyridin-2-yl-methanol

HRID 746613노트

반응식

HRID 746613 반응식
Br[C:2]1[C:3]2[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].CN(CCN(C)C)C.[Li]CCCC.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]=[O:36]>C1(C)C=CC=CC=1>[CH3:10][N:9]([CH3:11])[CH2:8][CH2:7][C:6]1[S:5][C:4]2[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=2[C:2]=1[CH:35]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=1)[OH:36]

참가 물질

6

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 142732-PyridinecarboxaldehydeHCID 58591562[2-(3-Bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amineHCID 178418339Butyllithium

생성물 1

HCID 11522497[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-pyridin-2-yl-methanol수율 82.4%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-78 °C

실험 절차

To a cooled (−78° C.) solution of [2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine (800 mg, 2.8 mmol) in anhydrous toluene (30 mL), TMEDA (420 uL, 2.8 mmol) was added followed by nBuLi (2.1 mL, 2.6 mmol, 1.6M in hexanes). The mixture was stirred for 40 min at −78° C. and pyridine-2-carbaldehyde (800 uL, 8.4 mmol) was added. The mixture was stirred for 6 hrs during which the temperature reached 0° C., quenched with sat NH4Cl/NaHCO3 and extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), concentrated and purified by silical gel column chromatography (gradient of DCM/MeOH=98/2 up to 94/6) to afford [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-pyridin-2-yl-methanol (Compound 13-1) (721 mg) in 82% yield. MH+=313.0, tR=2.49 min (Method 2).

후처리

  1. additionwas added
  2. stirringThe mixture was stirred for 6 hrs during which the temperature
  3. customreached 0° C.
  4. customquenched with sat NH4Cl/NaHCO3
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by silical gel column chromatography (gradient of DCM/MeOH=98/2 up to 94/6)

출처 및 근거

ORD 기록
ord-0bb4af0985c949b08158a8c2c93e507c
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393865B2

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