Sodium Carbonate → HCID 67970746, compound

HRID 1470753Notes

Reaction equation

HRID 1470753 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][C:10]=1[F:18])#[N:8].I[C:20]1[CH:21]=[N:22][C:23]([N:26]2[CH2:31][CH2:30][CH:29]([C:32]3[CH:37]=[CH:36][C:35]([C@@H:38]([NH:40][C:41](=[O:43])[CH3:42])[CH3:39])=[CH:34][CH:33]=3)[CH2:28][CH2:27]2)=[N:24][CH:25]=1>O1CCOCC1.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:20]2[CH:25]=[N:24][C:23]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]4[CH:37]=[CH:36][C:35]([C@@H:38]([NH:40][C:41](=[O:43])[CH3:42])[CH3:39])=[CH:34][CH:33]=4)[CH2:28][CH2:27]3)=[N:22][CH:21]=2)=[CH:11][C:10]=1[F:18])#[N:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 67125478HCID 67125478, compound2×

Product 1

HCID 67970746HCID 67970746, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Under argon atmosphere 0.1 mL sat. Na2CO3-solution and 3 mg (0.004 mmol) bis(triphenylphosphine)-palladium(II) chloride are added to a mixture of 16 mg (0.10 mmol) 4-cyano-3-fluorophenylboronic acid and 45 mg (0.10 mmol) (S)—N-(1-{4-[1-(5-iodopyrimidin-2-yl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (compound 4.43) in 2 mL dioxane/1 mL MeOH. The mixture was stirred at 70° C. for 6 h. After that time, the mixture was diluted with DMF and filtered. The filtrate was purified using reversed phase HPLC (water/MeOH, 0.1% TFA) to yield the desired product.

Workup

  1. filtrationfiltered
  2. customThe filtrate was purified

Sources & evidence

ORD record
ord-6604d32cf9c347e183d2114c6623b676
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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