Stannous chloride dihydrate → 4-(1-(2-methoxyethyl)-1H-pyrrolo[3,2-b]pyridin-7-ylthio)benzenamine

HRID 1042873Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[S:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH:7]=[CH:6]1.O.O.[Sn](Cl)Cl>CO>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[S:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH:7]=[CH:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

A sealed vial was charged with 1-(2-methoxyethyl)-7-(4-nitrophenylthio)-1H-pyrrolo[3,2-b]pyridine (0.147 g, 0.446 mmol) and methanol (5 mL). Tin (II) chloride dihydrate (0.504 g, 2.23 mmol) was added and the reaction was stirred at 50° C. for 3 hours. The reaction was concentrated and dissolved in DCM. The solution was washed with saturated sodium bicarbonate solution, which was extracted with DCM. The combined organic layers were washed with water, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (gradient elution 0-10% DCM:MeOH) to afford 4-(1-(2-methoxyethyl)-1H-pyrrolo[3,2-b]pyridin-7-ylthio)benzenamine as an orange oil that solidified under high vacuum. MS: M+H+=300.1.

Workup

concentrationThe reaction was concentrated
dissolutiondissolved in DCM
washThe solution was washed with saturated sodium bicarbonate solution, which
extractionwas extracted with DCM
washThe combined organic layers were washed with water
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe material was purified via column chromatography (gradient elution 0-10% DCM:MeOH)

Sources & evidence

ORD record: ord-d3a82f69a50340e1bb6e6cb75c437983
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557816B2

Reaction notes

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