Tetraethyltin → 1-Benzyl-3-chloro-7-ethyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642267Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:15]([Cl:16])=[CH:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10](Cl)[N:11]=1)=[O:5])[CH3:2].[CH2:25]([Sn](CC)(CC)CC)[CH3:26]>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:15]([Cl:16])=[CH:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10]([CH2:25][CH3:26])[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-benzyl-3,7-dichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (126.1 mg, 0.19 mmol), tetraethyltin (50 mg, 0.21 mmol), and Pd(PPh3)2Cl2 (6.7 mg, 0.0095 mmol) in DMF (1 mL) was stirred at 120° C. for 2.5 h. The mixture was then diluted with EtOAc, washed with water and saturated NaCl aqueous solution, respectively; the EtOAc phase was dried over anhydrous sodium sulfate, concentrated, and the residue was purified by column to give a white solid, the desired title compound. The title compound, ESI MS (m/z): 359 (M+H+).

Workup

washwashed with water and saturated NaCl aqueous solution
dry with materialthe EtOAc phase was dried over anhydrous sodium sulfate
concentrationconcentrated
customthe residue was purified by column
customto give a white solid

Sources & evidence

ORD record: ord-9d7de719575a4c759d5c66b0bc19d0dd
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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