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 602542노트

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HRID 602542 반응식
[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

참가 물질

5

반응물 4

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

생성물 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

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7fcf7ee75d784288916e4c28eea30789
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906528B2

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