Methanol → HCID 68328196, compound

HRID 634116Notes

Reaction equation

[I:1][C:2]1[C:6]2=[N:7][C:8]([C:11]([OH:13])=[O:12])=[CH:9][CH:10]=[C:5]2[N:4]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1.[C:24](Cl)(=O)C(Cl)=O.CO>C(Cl)Cl.CN(C=O)C>[I:1][C:2]1[C:6]2=[N:7][C:8]([C:11]([O:13][CH3:24])=[O:12])=[CH:9][CH:10]=[C:5]2[N:4]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid (0.750 g, 1.696 mmol) in DCM (8.5 mL) and a few drops of DMF was added oxalyl chloride (0.259 mL, 2.97 mmol) at RT. After 30 min, the reaction was cooled to 0° C., MeOH was added and the mixture was stirred for 30 min. The mixture was then concentrated. To the yellow solid was added H2O and the mixture was extracted with DCM (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give methyl 3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxylate (0.700 g, 1.534 mmol, 90%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 457.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 2.38 (3H, s), 4.01 (3H, s), 7.27-7.32 (2H, m), 7.75-7.81 (2H, m), 8.02 (1H, s), 8.18 (1H, d, J=8.80 Hz), 8.34 (1H, d, J=8.61 Hz).

Workup

concentrationThe mixture was then concentrated
additionTo the yellow solid was added H2O
extractionthe mixture was extracted with DCM (3×)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1bf358f941bb44ea8501820b337ef2d2
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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