Furan → HCID 23595361, compound

HRID 339157Notes

Reaction equation

O1C=CC=C1.Cl[C:7]1[N:8]=[C:9]2[CH:19]=[CH:18][O:17][C:10]2=[C:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2.[F-:20]>>[F:20][C:7]1[N:8]=[C:9]2[CH2:19][CH2:18][O:17][C:10]2=[C:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2

Participants

Reactant 3

HCID 8029Furan

HCID 28179Fluoride Ion

HCID 23595356HCID 23595356, compound

Product 1

HCID 23595361HCID 23595361, compound

Procedure

The chloride/fluoride exchange was achieved by the method (reference 3) cited above. Thus 90 mg of 5-chloro-2,3-dihydro-1-oxa-4-aza-cyclopenta[a]naphthalene (Example 217) was suspended in 1.5 mL of Bu4PHF2 and was irradiated under microwave (Smith Reactor) to about 120° C. for 2 hours. After aqueous work up and column purification, 22 mg of fluoride product was obtained (26.9%). LC/MS rt-min (MH+): 1.91 (190) [method B]. The furan derivative (Example 218), 5-chloro-1-oxa-4-aza-cyclopenta[a]naphthalene was sufficiently reactive to be alkylated with the tripeptide directly without fluoride activation.

Workup

customLC/MS rt-min (MH+)

Sources & evidence

ORD record: ord-f397c188a8fd428d9e81987410b786a0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889871B2

Reaction notes

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