Sodium hydride → HCID 118161790, compound

HRID 2203661Notes

Reaction equation

HRID 2203661 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH3:15].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH3:15])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 126752472-(1-Chloroethyl)pyridineHCID 242292566-Bromo-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 118161790HCID 118161790, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To an ice-cooled suspension of 6-bromo-1H-pyrrolo[3,2-b]pyridine (7.0 g, 35 mmol) in N,N-dimethylformamide (100 mL) was slowly added a solution of sodium hydride (2.12 g, 88.28 mmol, 60% in mineral oil) in N,N-dimethylformamide (20 mL). After 30 min at 0° C., a solution of 2-(1-chloroethyl)pyridine (5.0 g, 35 mmol) in N,N-dimethylformamide (20 mL) was slowly added. The mixture was then warmed to room temperature. After 16 h, saturated aqueous ammonium chloride solution (20 mL) was slowly added to the reaction mixture, and the resulting solution was concentrated in vacuo. The resulting residue was purified by flash column chromatography (10→30% ethyl acetate in petroleum ether) to afford 6-bromo-1-(1-(pyridin-2-yl)ethyl)-1H-pyrrolo[3,2-b]pyridine (6.0 g, 56% yield). 1H NMR (400 MHz, Chloroform-d) δ 8.61 (d, J=4.4 Hz, 1 H), 8.47 (d, J=2.0 Hz, 1 H), 7.70 (s, 1 H), 7.62-7.57 (m, 2 H), 7.21-7.18 (m, 1 H), 6.81-6.76 (m, 2 H), 5.66-5.61 (m, 1 H), 2.00 (d, J=7.2 Hz, 3 H).

Workup

  1. waitAfter 16 h
  2. concentrationthe resulting solution was concentrated in vacuo
  3. customThe resulting residue was purified by flash column chromatography (10→30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-85c9d07134494a6da897d72711ef9272
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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