Water → HCID 90093879, compound

HRID 1753055Notes

Reaction equation

HRID 1753055 reaction equation
[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:18]([CH3:20])[CH3:19].O>CN(C=O)C>[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:18]([CH3:20])[CH3:19])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 116873853-IODO-1H-PYRROLO[3,2-C]PYRIDINE

Product 1

HCID 90093879HCID 90093879, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-iodo-1H-pyrrolo[3,2-c]pyridine (Preparation 47, 82 g, 340 mmol) and cesium carbonate (164 g, 504 mmol) in DMF (650 mL) was added 2-iodopropane (30.7 mL, 307 mmol) dropwise over 25 minutes at room temperature and the reaction was stirred for 6 hours. The reaction was poured into water (500 mL), stirred for 10 minutes and extracted into EtOAc (4×350 mL). The organic layers were combined, washed with brine, passed through a phase separation cartridge and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with DCM followed by 50% EtOAc in DCM to afford the title compound as a pale brown gum (93 g, 61%).

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted into EtOAc (4×350 mL)
  3. washwashed with brine
  4. custompassed through a phase separation cartridge
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. washeluting with DCM

Sources & evidence

ORD record
ord-bf92c5d45b1a47beb80c26a7fd583688
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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