Hydrochloric Acid → 2,3-Dimethyl-5-methylthio-7-phenacylpyrrolo[2,3-b]pyridine

HRID 1756072Notes

Reaction equation

[CH3:1][C:2]1[NH:12][C:5]2=[N:6][CH:7]=[C:8]([S:10][CH3:11])[CH:9]=[C:4]2[C:3]=1[CH3:13].CC1NC2=NC(SC)=CC=C2C=1C.[CH2:27](Cl)[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].Cl>>[CH3:1][C:2]1[N:12]=[C:5]2[N:6]([CH2:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:29])[CH:7]=[C:8]([S:10][CH3:11])[CH:9]=[C:4]2[C:3]=1[CH3:13]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 107572-Chloroacetophenone

HCID 193926102,3-Dimethyl-6-mehylthiopyrrolo[2,3-b]pyridine

HCID 199168232,3-Dimethyl-5-methylthiopyrrolo[2,3-b]pyridine

Product 1

HCID 199167972,3-Dimethyl-5-methylthio-7-phenacylpyrrolo[2,3-b]pyridineYield 63%

Procedure

The title compound was prepared on a 0.6 mmol scale from 2,3-dimethyl-5-methylthiopyrrolo[2,3-b]pyridine (prepared according to the procedure described for 2,3-dimethyl-6-methylthio-pyrrolo[2,3-b]pyridine) and phenacyl chloride as described in Example 43 yielding 140 mg (63%) pure title compound as the hydrochloride.

Workup

customprepared

Sources & evidence

ORD record: ord-3d14531c529746d9b83f1643dae5288f
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05439917

Reaction notes

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