Pyrrole → 2-tert-butyl-1H-pyrrole

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6](Cl)([CH3:9])([CH3:8])[CH3:7]>>[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

Reactant 2

HCID 8027Pyrrole

HCID 10486tert-BUTYL CHLORIDE

Product 1

HCID 2209452-tert-butyl-1H-pyrrole

Procedure

wherein X1, X2, Z, and R1 are as defined above. The pyrrole can reacted with t-butylchloride under Friedel-Craft alkylation condition to give the tert-butylpyrrole 2, which can then be nitrated. The ester is then hydrolyzed, e.g., with LiOH, and coupled to give amide 4. Compound 4 is then reduced to give the amine which is reacted with isocyanate to give compound 5, which is an exemplary compound of Formula I.

Sources & evidence

ORD record: ord-d186af39bc454bfbb254c01971098a77
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741479B2

Reaction notes

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