Iodoethane → HCID 852077, compound

HRID 2196709Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]1([S:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3C=C2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.ICC.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH2:3]([C:2]1[N:15]([S:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:14])=[O:13])[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[CH:1]=1)[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (2.03 mL, 3.25 mmol, 1.6M in hexanes) was added to a solution of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.60 g, 2.32 mmol) in THF (9.0 mL) at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes, and then iodoethane (0.557 mL, 6.97 mmol) was added. The reaction mixture was warmed up to 0° C. and stirred for 2 hours, after which more iodoethane (0.278 mL, 3.48 mmol) was added. The reaction mixture was warmed up to room temperature and stirred overnight. Saturated aqueous ammonium chloride and ethyl acetate were then added, and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford 2-ethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.25 g, 23% yield).

Workup

temperatureThe reaction mixture was warmed up to 0° C.
stirringstirred for 2 hours
temperatureThe reaction mixture was warmed up to room temperature
stirringstirred overnight
customthe layers were separated
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organic layers were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-e790c6767941439a94b4498f41b8dcb5
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

Loading…