Sodium hydride → HCID 57985912, compound

HRID 1869214Notes

Reaction equation

HRID 1869214 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[H-].[Na+].[Cl:13][CH2:14][CH2:15][CH:16](OS(C)(=O)=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:14][Cl:13])[CH:9]=[CH:10][C:3]=12.[Cl:1][C:2]1[C:3]2=[C:4]3[N+:5]([CH2:14][CH2:15][CH:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:8]3[CH:9]=[CH:10]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 57985877Methanesulfonic acid 3-chloro-1-phenyl-propyl ester

Product 2

HCID 57985912HCID 57985912, compoundHCID 57985920HCID 57985920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a RT solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine (200 mg, 1.31 mmol) in DMF (5 mL) was added NaH (60% in mineral oil, 57.7 mg, 1.44 mmol) followed by methanesulfonic acid 3-chloro-1-phenyl-propyl ester (326 mg, 1.31 mmol). The reaction mixture was stirred at RT overnight, poured into ice-water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to yield 4-Chloro-1-(3-chloro-1-phenyl-propyl)-1H-pyrrolo[2,3-b]pyridine as a mixture with the cyclization product 8-Chloro-3-phenyl-4,5-dihydro-3H-2a-aza-5a-azonia-acenaphthylene. The mixture was used in the next step without purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a0079ea18e0481aa391155e58b7a22e
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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