Trimethylsilyl iodide → HCID 178519785, compound
Reaction equation
[I:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10]C)[N:5]=[CH:4][CH:3]=1.I[Si](C)(C)C>>[OH:10][C:6]1[N:5]=[CH:4][CH:3]=[C:2]([I:1])[C:7]=1[CH:8]=[O:9]Participants
Procedure
In another embodiment, general acid 2 can be prepared from an acid of formula 40 as illustrated in Scheme 7. Thus, 4-iodo-2-methoxynicotinaldehyde (37; See: WO95/29917) is de-methylated, for example by treatment with iodotrimethylsilane, to provide 2-hydroxy-4-iodonicotinaldehyde (38). Reacton of 38 with arylboronic acid 34 in the presence of copper(II) acetate and pyridine affords N-aryl pyridone aldehyde 39. Oxidation of 39 using sodium chlorite provides acid 40. Alternately, treatment of methyl 2-hydroxy-4-iodonicotinate (41) with arylboronic acid 34 in the presence of copper(II) acetate and pyridine affords N-aryl pyridone ester 42. Saponification of 42 under standard conditions, for example sodium hydroxide, affords acid 40. Treatment of iodo acid 40 with a compound of formula 20, optionally in the presence of a base, for example potassium carbonate, and/or optionally with heating, provides acid 2. Additionally, acid 40 can be used as a general example of acid 17 (W is Iodo, Scheme 3).
Sources & evidence
- ORD record
- ord-00eb3e4be25348d0ad9a943dc58f4c71
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921565B2
Reaction notes
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