Triphenylphosphine → HCID 178510371, compound

HRID 1802590Notes

Reaction equation

[N-]=[N+]=[N-].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:24]([CH2:27][C:28]1[N:29]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]3=[O:45])=[CH:35][C:34]=2[F:46])[NH:31][CH:32]=1)=[N+]=[N-]>>[NH2:24][CH2:27][C:28]1[N:29]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]3=[O:45])=[CH:35][C:34]=2[F:46])[NH:31][CH:32]=1

Participants

Reactant 3

HCID 11776Triphenylphosphine

HCID 33557Sodium Azide

HCID 178514574HCID 178514574, compound2×

Product 1

HCID 178510371HCID 178510371, compound

Procedure

Alternatively as shown in Scheme 4,1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene 3-2 prepared as above, is treated with 4-hydroxymethylimidazole II-1 in the presence of 8-hydroxyquinoline, and K2CO3 in DMSO. The resulting mixture is degassed before being charged with CuI to give 4-hydroxymethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole 4-1. The compound 4-1 is treated with thionyl chloride to give 4-chloromethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole which is then treated with NaN3 to result in 4-azidomethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole 4-2. The azide 4-2 is reduced with Ph3P to give 4-aminomethyl-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)imidazole 4-3. The compound 4-3 is then treated with 5-chlorothiophene-2-carboxylic acid 1-5 to give the title compound 21.

Sources & evidence

ORD record: ord-2e901bf3a57d4589a533d232b0690347
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349873B2

Reaction notes

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