4-Chloro-3-iodopyridin-2-amine → Methyl 1-chloro-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylate

HRID 1029224Notes

Reaction equation

HRID 1029224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1I.CC1(C)C(C)(C)OB([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[C:28](OC)=[O:29])O1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:3]=1[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[C:28](=[O:29])[NH:8]2

Participants

3

Reactant 2

HCID 229365964-Chloro-3-iodopyridin-2-amineHCID 68648791Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate

Product 1

HCID 58168369Methyl 1-chloro-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylateYield 48.5%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 1 using 4-chloro-3-iodopyridin-2-amine (510 mg, 2.0 mmol) and dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate (705 mg, 2.2 mmol) to provide 266 (280 mg, 48% yield) as a white solid. LC-MS (M+H=289, obsd.=289).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-b33068174aa14663b971489d5dc782fb
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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