Diethyl Ether → HCID 57893465, compound

HRID 1821836Notes

Reaction equation

HRID 1821836 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH:11]=[O:12])[NH:8][C:7]=12.[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOCC.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]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:7]=12

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 578935647-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbaldehydeHCID 178418255HCID 178418255, compound2×

Product 1

HCID 57893465HCID 57893465, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 138) (1.0 g, 5.5 mmol) in THF (27.7 mL) was added 3.0 M phenylmagnesium bromide in Et2O (3.8 mL, 11.3 mmol) at −78° C. under a nitrogen atmosphere. After stirring for ca. 2 h, additional 3.0 M phenylmagnesium bromide in Et2O (0.92 mL, 2.7 mmol) was added. The reaction mixture was stirred for another 1.5 h. The reaction mixture was poured into a saturated NH4Cl solution and extracted with EtOAc (3×). The combined organic extracts were washed with saturated NaCl, and dried over Na2SO4. Filtration and concentration provided the crude material, which was purified by flash chromatography to provide (7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (0.97 g, 67%) as an off-white solid: 1H NMR (300 MHz, CD3OD) δ5.99 (1H, s), 6.42 (1H, s), 7.25-7.48 (6H, m), 7.82 (1H, d, J=5.4 Hz); ESI MS m/z 259 [C14H11ClN2O+H]+; HPLC (Method A) >99% (AUC), tR=13.8 min.

Workup

  1. stirringThe reaction mixture was stirred for another 1.5 h
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic extracts were washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and concentration
  6. customprovided the crude material, which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-63589a936e79420986b74cdb01fd4f1a
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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