Dimethylformamide → HCID 59436081, compound

HRID 1802502Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][N:23]=[C:24]([O:25][CH3:26])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1.[CH3:27][N:28](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][N:23]=[C:24]([O:25][CH3:26])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1)[C:27]#[N:28]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-(2,6-dichloro-4-iodophenyl)-10-methoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (Example 152, Step 1) (1.0 g, 2.01 mmol) in DMF (10 mL) was added zinc cyanide (283 mg, 2.41 mmol) and Pd(Ph3P)4 (465 mg, 0.402 mmol). The reaction was stirred at 80 ° C. for 2.5 h in a sealed tube. After cooling to room temperature, the reaction was diluted with ethyl acetate and washed with water followed by brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with methanol in dichloromethane to afford the title compound.

Workup

temperatureAfter cooling to room temperature
washwashed with water
dry with materialThe organic layer was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel eluting with methanol in dichloromethane

Sources & evidence

ORD record: ord-2cc2dc4237e44d509d7f1738f388b5cf
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

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