1,2-Dibromoethane → HCID 86720570, compound

HRID 513189Notes

Reaction equation

HRID 513189 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[CH:16]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[NH:18][C:14]=3[CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2].[H-].[Na+].[Br:25][CH2:26][CH2:27]Br>CN(C=O)C.O>[Br:25][CH2:26][CH2:27][N:18]1[C:14]2[CH:13]=[CH:12][N:11]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)[C:15]=2[CH:16]=[C:17]1[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 71212553HCID 71212553, compound

Product 1

HCID 86720570HCID 86720570, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(3-ethoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (230 mg, 0.776 mmole) in DMF (7 mL) was added NaH (60% dispersion in mineral oil, 40 mg, 1.000 mmole) at RT. After gas evolution had ceased 1,2-dibromoethane (1 mL, 11.60 mmole) was added rapidly. After stirring overnight the mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were washed with H2O and brine then dried (MgSO4), filtered, and concentrated. Flash column (Biotage-SNAP-25 g SiO2, 0-50% EtOAc/hexanes) gave the title compound (135 mg, 43%) as a clear gum. 1H NMR (400 MHz, CDCl3): δ8.51 (d, J=6.0 Hz, 1 H); 7.60 (d, J=1.0 Hz, 1 H); 7.49-7.45 (m, 2 H); 7.40 (m, J=7.9 Hz, 1 H); 7.31 (dd, J=6.0, 1.0 Hz, 1 H); 6.99 (ddd, J=8.2, 2.6, 1.1 Hz, 1 H); 4.92 (t, J=6.83 Hz, 2 H); 4.12 (q, J=7.0 Hz, 2 H); 3.91 (s, 3 H); 3.71 (t, J=7.12 Hz, 2 H); 1.43 (t, J=7.12 Hz, 2 H).

Workup

  1. additionwas added rapidly
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c744f6f0088c410f89c923e19f7b71de
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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