Dimethylformamide → HCID 10186267, compound

HRID 971111Notes

Reaction equation

[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[C:22]([Br:24])[CH:21]=[C:20](Br)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[CH3:26][N:27]([CH3:30])C=O>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[CH:1]1([NH:4][C:5]([C:7]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:18]3[CH:23]=[C:22]([Br:24])[CH:21]=[C:20]([C:2]4[CH:30]=[N:27][C:26]([C:16]([OH:17])([CH3:7])[CH3:15])=[CH:3][CH:1]=4)[CH:19]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of N-cyclopropyl-1-(3,5-dibromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from Step 2,2-(1-hydroxy-1-methylethyl)-5-tributylstannylpyridine from Step 3 (1.4 eq), 1,1′-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq), and cuprous iodide (0.05 eq) in N,N-dimethylformamide (15 ml/mmol) was stirred at 85° C. for 5 hours. After cooling the resulting mixture was partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with a 1:6:3 mixture of ethanol, ethyl acetate and methylene chloride to afford the N-Cyclopropyl-1-{5-bromo-3-[6-(1-hydroxy-1-methylethyl)pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid.

Workup

temperatureAfter cooling the resulting mixture
customwas partitioned between ethyl acetate and water
customThe crude product from the organic phase was chromatographed on silica gel eluting with a 1:6:3 mixture of ethanol, ethyl acetate and methylene chloride

Sources & evidence

ORD record: ord-ae9bd96d7ac74ecf81b05c9f3bf461ce
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312334B2

Reaction notes

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