Phenylboronic Acid → HCID 68899647, compound
Reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10](I)=[N:11][NH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:11][NH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
In Scheme I, fluoronitrotoluene a is reacted with phenol b in the presence of mild base such as potassium carbonate, to afford a phenoxy nitrotoluene c. Phenoxy nitrotoluene c is then reduced, using catalyzed hyrdogenation or othe reduction technique, to provide phenoxy aminotoluene d. Phenoxy aminotoluene d undergoes a cyclization reaction by treatment with isoamyl nitrate to form phenoxy indazole e. Phenoxy indazole e is subject to iodine under basic conditions to yield a phenoxy iodoindazine f, which is then protected via Boc, Fmoc or other suitable protection scheme, to afford a protected phenoxy iodoindazole g. The protected phenoxy iodoindazole g is treated with a phenyl boronic acid h in the presence of a suitable catalyst to form a phenoxy phenylindazole i, which is deprotected to provide an indazole derivative j in accordance with the invention.
Sources & evidence
- ORD record
- ord-93b4893582a3444997964b475ec5e2c5
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495015B2
Reaction notes
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