Diethyl Ether → HCID 57893459, compound

HRID 1821914Notes

Reaction equation

HRID 1821914 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH:11]=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1.[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)C.[Cl-].[NH4+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[OH:12])[NH:8][C:5]2=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 76851465HCID 76851465, compoundHCID 178418255HCID 178418255, compound2×

Product 1

HCID 57893459HCID 57893459, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (156 mg, 0.86 mmol) in tetrahydrofuran (5 mL) was added 3.0 M phenylmagnesium bromide in diethyl ether (0.58 mL, 1.74 mmol) at −78° C. under a nitrogen atmosphere. The reaction mixture was slowly warmed to −15° C. After stirring for ca. 5 h, additional 3.0 M phenylmagnesium bromide in diethyl ether (0.15 mL, 0.45 mmol) was added. The reaction mixture was stirred for another 1 h, warming to 0° C. The reaction mixture was poured into a 2:1 solution of saturated ammonium chloride and water, and extracted with ethyl acetate (3×). The combined organic extracts were washed with water and brine, and dried over sodium sulfate. After filtration and concentration, the crude product was purified by Biotage chromatography (1 to 100% ethyl acetate in hexanes) to give (5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (109 mg, 49%) as a yellow foam: 1H NMR (300 MHz, CDCl3) 8.69 (1H, s), 6.23 (1H, s), 7.33-7.61 (6H, m), 8.49 (1H, s), 8.69 (1H, br s); ESI MS m/z 259 [C14H11ClN2O+H]+.

Workup

  1. stirringThe reaction mixture was stirred for another 1 h
  2. temperaturewarming to 0° C
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe crude product was purified by Biotage chromatography (1 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2e56adaadb1349ad93bfec97353b9d94
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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