Carbon Tetrachloride → tert-Butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 240467Notes

Reaction equation

HRID 240467 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[C:10]([CH2:17]O)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[C:10]([CH2:17][Cl:39])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 49758903tert-Butyl 3-(hydroxymethyl)-1H-pyrrolo(2,3-b)pyridine-1-carboxylate

Product 1

HCID 21463021tert-Butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(tert-butyloxycarbonyl)-3-(hydroxymethyl)-7-azaindole (Int-17, 8.4 g, 34 mmol), triphenylphosphine (9.9 g, 37 mmol), dry CCl4 (50 mL) in dry DMF (35 mL) were stirred at room temperature for 48 h. Solvents were removed and the residue was purified by flash column chromatography to give chloride Int-14 (3.45 g, 38%).

Workup

  1. customSolvents were removed
  2. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-32715abe7a8042a9a9999a90659dda8c
Source dataset
uspto-grants-2014_02
Patent number
US08648086B2

Reaction notes

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