Potassium Carbonate → HCID 67083815, compound

HRID 2239525Notes

Reaction equation

HRID 2239525 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[N:7][C:6]([C:14]#[N:15])=[C:5]2[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[F:24].[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.O.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>[F:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:5]1[C:4]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:2]([C:28]3[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=3)[CH:3]=2)[N:8]=[N:7][C:6]=1[C:14]#[N:15]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 67083712HCID 67083712, compound

Product 1

HCID 67083815HCID 67083815, compoundYield 69.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 6-bromo-4-(2-fluoro-4-methylphenylamino)-7-methoxycinnoline-3-carbonitrile (Method 38, 0.25 g, 0.65 mmol), pyridin-4-ylboronic acid (0.159 g, 1.29 mmol) and K2CO3 (0.357 g, 2.58 mmol) in DMA (3.0 ml) and water (0.30 ml), was added Pd(Ph3P)4 (0.224 g, 0.19 mmol). The reaction was stirred under argon at 90° C. for 12 hours, cooled, diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic extract was dried (MgSO4), filtered, and the residue purified with silica chromatography (EtOAc) to give 0.175 g (64%) product. m/z 386.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc (2×50 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customthe residue purified with silica chromatography (EtOAc)

Sources & evidence

ORD record
ord-0722508162fc4ac09425e26f9699d71c
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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