Oxalyl chloride → HCID 86760497, compound

HRID 1766159Notes

Reaction equation

[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH3:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[C:19]([C:26]([OH:28])=[O:27])=[CH:18]2)=[CH:13][CH:12]=1)(=[O:10])=[O:9]>ClCCl>[CH3:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[C:19]([C:26]([O:28][C:1]([C:2]3[C:20]4[C:21](=[N:22][CH:23]=[CH:24][CH:25]=4)[N:17]([C:14]4[CH:15]=[CH:16][C:11]([S:8]([CH3:7])(=[O:10])=[O:9])=[CH:12][CH:13]=4)[CH:18]=3)=[O:5])=[O:27])=[CH:18]2)=[CH:13][CH:12]=1)(=[O:9])=[O:10]

Participants

Conditions

Temperature: 20 °C

Procedure

0.52 cm3 (6 mmol) of oxalyl chloride was added, under an argon atmosphere, to 1-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid in 15 cm3 of dichloromethane. After stirring at a temperature in the region of 20° C. for 300 h, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa). The residue was triturated with 20 cm3 of dichloromethane, filtered and pulled dry, and then the solid was washed with 50 cm3 of distilled water to give, after drying, 0.13 g of bis[1-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic]anhydride in the form of a powder which was used directly in the following stage. IR spectrum (KBr): 3116, 2926, 1767, 1705, 1592, 1537, 1421, 1294, 1177, 1151, 1083, 999, 962, 775, 551 and 532 cm−1.

Workup

concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
customThe residue was triturated with 20 cm3 of dichloromethane
filtrationfiltered
custompulled dry
washthe solid was washed with 50 cm3 of distilled water
customto give
customafter drying

Sources & evidence

ORD record: ord-b91a090887c2445080afc1d545e793ee
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230007B2

Reaction notes

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