Diethyl Ether → HCID 57893455, compound

HRID 1821849

Reaction equation

HRID 1821849 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH:18]=[O:19])[NH:15][C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([Mg]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOCC.[Cl-].[NH4+]>O1CCCC1>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[OH:19])[NH:15][C:14]=12)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 578935037-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehydeHCID 178418255HCID 178418255, compound2×

Product 1

HCID 57893455HCID 57893455, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 141) (1.7 g, 5.1 mmol) in tetrahydrofuran (25 mL) was added 3.0 M phenylmagnesium bromide in Et2O (2.0 mL, 6 mmol) dropwise at −78° C. under a nitrogen atmosphere. After stirring for ca. 2 h, additional 3.0 M phenylmagnesium bromide in Et2O (2.0 mL, 6 mmol) was added. The reaction mixture was stirred for another 1.5 h warming to −15° C. The reaction mixture was poured into a saturated ammonium chloride solution, and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated sodium chloride, and dried over sodium sulfate. Filtration and concentration provided the crude material, which was purified by Biotage chromatography (10-30% ethyl acetate in hexanes) to provide [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol (1.32 g, 62%) as a yellow foam: mp 53-61° C.; 1H NMR (500 MHz, CD3OD) δ4.60 (4H, q, J=23.2, 15.4 Hz), 5.95 (1H, s), 6.25 (1H, s), 7.05 (1H, d, J=5.7 Hz), 7.15-7.40 (15H, m), 7.62 (1H, d, J=5.7 Hz); ESI MS m/z 420 [C28H25N3O+H]+; HPLC (Method A) >99% (AUC), tR=19.2 min.

Workup

  1. stirringThe reaction mixture was stirred for another 1.5 h
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration
  6. customprovided the crude material, which
  7. customwas purified by Biotage chromatography (10-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e8ef13baa8f14ab4b618b086164db16e
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Linked notes

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