Diethyl Ether → HCID 57893488, compound

HRID 1821855Notes

Reaction equation

HRID 1821855 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[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]=[O:19])[NH:15][C:12]2=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Mg]Br.C(OCC)C.[NH4+].[Cl-]>O1CCCC1>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]([OH:19])[CH3:27])[NH:15][C:12]2=[CH:13][N:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 57893538HCID 57893538, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57893488HCID 57893488, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 139) (2.89 g, 8.46 mmol) in tetrahydrofuran (42 mL) was added 3.0 M methylmagnesium bromide in diethyl ether (7.05 mL, 21.2 mmol). The reaction mixture was stirred overnight (16 h) under a nitrogen atmosphere at room temperature. The reaction mixture was poured into a stirring saturated NH4Cl solution. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic extracts were dried over Na2SO4. After filtration and concentration, a small amount of the desired product was obtained by trituration with CH2Cl2. Additional material was obtained by purification using Biotage chromatography on silica (eluting with Hex/EtOAc 90:10 to 0:100) to provide 1-[5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]ethanol (1.74 g, 57%) as an off-white solid: 1H NMR (300 MHz, CD3OD) δ1.53 (3H, d, J=6.6 Hz), 4.69 (4H, s), 4.90-4.99 (1H, m), 6.08 (1H, s), 6.58 (1H, s), 7.17-7.29 (10H, m), 8.26 (1H, s); ESI MS m/z 358 [C23H23N3O+H]+; HPLC (Method A) 98.5% (AUC), tR=18.2 min.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-662058b820044f2496196f1ec40b2584
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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