Ethyl Bromide → HCID 69275385, compound

HRID 2375408Notes

Reaction equation

[C:1]([C:4]1[C:5]([C:20](=[O:22])[CH3:21])=[C:6]([CH3:19])[N:7]([C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[CH:12][C:11]=2[CH3:18])[C:8]=1[CH3:9])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][CH3:31]>>[C:1]([C:4]1[C:5]([C:20](=[O:22])[CH3:21])=[C:6]([CH3:19])[N:7]([C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([O:17][CH2:30][CH3:31])=[CH:12][C:11]=2[CH3:18])[C:8]=1[CH3:9])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 6332Ethyl Bromide

HCID 11430Potassium Carbonate

HCID 69274136HCID 69274136, compound

Product 1

HCID 69275385HCID 69275385, compound

Procedure

Utilizing the general procedure outlined in Example 7, 1-[4-acetyl-1-(4-hydroxy-2,5-dimethyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (100 mg, 0.3 mmol) reacted with bromoethane (300 μL, excess), in the presence of K2CO3 (50 mg), to afford 1-[4-acetyl-1-(4-ethoxy-2,5-dimethyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone: MS (ESI) 328 (M+H)+. Utilizing the general procedure outlined in Example 48, 1-[4-acetyl-1-(4-ethoxy-2,5-dimethyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (108 mg, 0.3) and hydrazine (50 μL) reacted to give 6-(4-Ethoxy-2,3-dimethyl-phenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]-pyridazine as an off-white solid: 1H NMR (CDCl3, 500 MHz) δ 6.88 (s, 1H), 6.77 (s, 1H), 4.14 (q, 2H), 2.85 (s, 6H), 2.39 (s, 6H), 2.26 (s, 3H), 1.83 (s, 3H, 1.50 (t, 3H); MS (ESI) 324 (M+H)+.

Sources & evidence

ORD record: ord-4e5415e224054230be24a6dccd08d649
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465730B2

Reaction notes

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