Potassium Carbonate → 2-bromo-5-chloro-1-(3-chlorobenzyl)-1H-pyrrolo[3,2-b]pyridine

HRID 628364Notes

Reaction equation

HRID 628364 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1.[Br:16][C:17]1[NH:25][C:24]2[C:19](=[N:20][C:21]([Cl:26])=[CH:22][CH:23]=2)[CH:18]=1>CN(C=O)C.C(OCC)(=O)C>[Br:16][C:17]1[N:25]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[C:24]2[C:19](=[N:20][C:21]([Cl:26])=[CH:22][CH:23]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 1181597982-bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 1181598922-bromo-5-chloro-1-(3-chlorobenzyl)-1H-pyrrolo[3,2-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

K2CO3 (0.97 g, 7.0 mmol) and 1-(bromomethyl)-3-chlorobenzene (0.74 mL, 5.6 mmol, Aldrich) were added to a solution of 2-bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine (1.5 g, 4.7 mmol, from Step 1) in DMF (20 mL). After a reaction time of 75 minutes, the reaction was diluted with ethyl acetate and washed with water three times, followed by one wash with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. Flash chromatography, loading in DCM, eluting with a gradient from 0-10% EtOAc in hexanes, afforded product as a white solid. Yield (1.3 g, 70%).

Workup

  1. washwashed with water three times
  2. washwash with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washFlash chromatography, loading in DCM, eluting with a gradient from 0-10% EtOAc in hexanes
  7. customafforded product as a white solid
  8. customYield (1.3 g, 70%)

Sources & evidence

ORD record
ord-e9a3d5b23f4346ec9cd9e1ee4408d671
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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