Water → HCID 57537462, compound

HRID 1693701Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:12][S-:13].[Na+].O>CN(C=O)C>[Br:1][C:2]1[C:3]([S:13][CH3:12])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.16 mmol) was combined with sodium thiomethoxide (151 mg, 2.16 mmol) and dissolved in N,N-dimethylformaldehyde (5 mL). The solution was at 80° C. for 15 hours when additional sodium thiomethoxide (75 mg, 1.08 mmol) was added. The solution was stirred for at 80° C. for 2 hours. Water (50 mL) was added to the reaction mixture, and the precipitate was collected by vacuum filtration to afford 5-Bromo-4-methylsulfanyl-1H-pyrrolo[2,3-b]pyridine (524 mg, 2.16 mmol, >99% yield) as a white solid. 1H-NMR [500 MHz, d6-DMSO] δ: 11.99 (s, 1H), 8.22 (s, 1H), 7.54 (d, 1H), 6.69 (d, 1H), 2.74 (s, 3H); MS [MH+] m/z: 243.0, 244.9

Workup

filtrationthe precipitate was collected by vacuum filtration

Sources & evidence

ORD record: ord-16b55e095ca24483ba18b19310ac9e3a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158647B2

Reaction notes

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