Tetrahydrofuran → 1-[5-(2,6-dimethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3-methyl-butan-1-ol

HRID 602542ノート

反応式

HRID 602542 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5](CC)[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH:20]=[O:21])=[CH:18][N:17]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[C:14]2=[CH:15][N:16]=1)C.[CH2:31]([Mg]Cl)[CH:32]([CH3:34])[CH3:33].[NH4+].[Cl-].[CH2:39]1COCC1>>[CH3:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:39])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH:20]([OH:21])[CH2:31][CH:32]([CH3:34])[CH3:33])=[CH:18][N:17]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:29])[CH3:30])=[CH:24][CH:23]=3)[C:14]2=[CH:15][N:16]=1

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 866240795-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-carbaldehydeHCID 178418368HCID 178418368、化合物

生成物 1

HCID 671523991-[5-(2,6-dimethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3-methyl-butan-1-ol

反応条件

温度
-78 °C

実験手順

To a solution of 5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (50 mg, 0.13 mmol, prepared by the procedure described in Example 11, Step 3) in THF (2 mL) at −78° C., iso-butylmagnesium chloride (1M solution in THF, 300 μL, 0.32 mmol) is added. The mixture is stirred at −78° C. for two hours and is subsequently allowed to warm to room temperature. A saturated aqueous NH4Cl solution (5 mL) is added, and THF is removed under reduced pressure. The product is extracted with EtOAc. The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography of the residue affords 1-[5-(2,6-dimethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3-methyl-butan-1-ol as colorless oil. 1H NMR: (CDCl3) 8.97 (s, 1H), 7.64 (s, 1H), 7.9 (s, 1H), 7.48 (d, J=120 Hz, 2H), 7.41 (d, J=10 Hz, 2H), 7.29 (t, J=10 Hz, 1H), 7.15 (d, J=12 Hz, 2H), 5.13 (m, 1H), 3.95 (m, 1H), 2.44 (m, 4H), 1.34 (d, J=14 Hz, 6H), 1.04 (t, J=10 Hz, 6H); LCMS m/z 455.34 (2.58 min).

後処理

  1. customat −78° C.
  2. temperatureto warm to room temperature
  3. customTHF is removed under reduced pressure
  4. extractionThe product is extracted with EtOAc
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7fcf7ee75d784288916e4c28eea30789
出典データセット
uspto-grants-2011_03
特許番号
US07906528B2

反応ノート

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