Chlorosuccinimide → 1-Benzyl-3-chloro-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642414Notes

Reaction equation

HRID 642414 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Cl:36])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:8]2[C:14]([Cl:36])=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 684273231-Benzyl-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684289301-Benzyl-3-chloro-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 91.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-benzyl-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (67 mg, 0.176 mmol), NCS (28 mg), BzOOBz (2.3 mg) in carbon tetrachloride (2 mL) was refluxed for 1 h; then cooled, solvent was removed and the residue was purified with column to give the desired product (67 mg). 1H NMR (200 MHz, CDCl3): δ (ppm)=8.63 (s, 1H), 7.4-7.2 (m, 6H), 5.35 (s, 2H), 4.41 (q, J=7.1 Hz), 1.46 (s, 9H), 1.41 (t, 3H, J=7.1 Hz).

Workup

  1. temperaturewas refluxed for 1 h
  2. temperaturethen cooled
  3. customsolvent was removed
  4. customthe residue was purified with column

Sources & evidence

ORD record
ord-f647f3fd5a3d48389d6e39fea1bfdf24
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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