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

HRID 711298Notes

Reaction equation

HRID 711298 reaction equation
O[CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:39]>CN(C=O)C>[Cl:39][CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:4]=1

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-carboxylateYield 8.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (270 mg, 1.09 mmol) in 2.5 mL DMF was added triphenylphospine (285 mg, 1.09 mmol) and carbon tetrachloride (167 mg, 1.09 mmol). The reaction was allowed to stir 16 h at ambient temperature. The solution was concentrated and purified by silica gel chromatography (0-50% ethylacetate/hexanes) to give tert-butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (8.6%). 1H NMR (400 MHz, CDCl3): δ 8.56-8.55 (d, J=4.9 Hz, 1H), 8.02-8.00 (d, J=8.1 Hz, 1H), 7.69 (s, 1H), 7.26-7.24 (m, 1H), 5.30 (s, 2H), 1.54 (s, 9H).

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by silica gel chromatography (0-50% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-8f4164b97a4f401d8d7cdf359f4372ac
Source dataset
uspto-grants-2015_11
Patent number
US09181261B2

Reaction notes

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