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

HRID 746613ノート

反応式

HRID 746613 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0bb4af0985c949b08158a8c2c93e507c
出典データセット
uspto-grants-2008_07
特許番号
US07393865B2

反応ノート

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