2-Iodobenzoic acid → 3-Phenyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

HRID 498051Notes

Reaction equation

I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:11]1([C:17]2[CH:21]=[C:20]([NH2:22])[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(CC#N)(=O)C1C=CC=CC=1.N(C1C=CC=CN=1)N>>[C:11]1([C:17]2[C:21]3[C:4](=[O:6])[C:3]4[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:22][C:20]=3[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:18]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Reactant 4

HCID 69412-Iodobenzoic acid

HCID 64799Benzoylacetonitrile

HCID 786452-Hydrazinopyridine

HCID 122881361-pyridyl-3-phenyl-5-aminopyrazole

Product 1

HCID 1358480723-Phenyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

Procedure

Following the procedures described in Reference Example 2-5 and Example 2-12, the title compound was prepared from o-iodobenzoic acid and 3-phenyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine which was previously prepared from benzoylacetonitrile and 2-hydrazinopyridine following the method described in Reference Example 2-72 (58% yield).

Sources & evidence

ORD record: ord-2d0d0910f2d34f18aedcdc96b631b276
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949648B2

Reaction notes

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