Sodium Carbonate → HCID 69936331, compound

HRID 1623840Notes

Reaction equation

HRID 1623840 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([F:16])[CH:15]=1)=[O:8].[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCOCC1>[F:16][C:14]1[CH:15]=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:17]=[C:2]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)[CH:3]=[CH:4][C:5]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:11]=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 67107393HCID 67107393, compound

Product 1

HCID 69936331HCID 69936331, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a microwave vial was added 5-bromo-N-(5-fluoro-3-pyridinyl)-2-[(phenylmethyl)oxy]benzamide (may be prepared as described in Example 98; 200 mg, 0.50 mmol), 1,4-dioxane (2 ml), 4-pyridinylboronic acid (73.5 mg, 0.60 mmol), 1M sodium carbonate (1.00 ml, 1.00 mmol) and tetrakis(triphenylphosphine)palladium(0) (34.6 mg, 0.03 mmol). The vial was sealed and heated to 130° C. for 30 min under microwave conditions. The mixture was evaporated under reduced pressure and the residue was purified using MDAP (twice) to yield the title compound. 9 mg.

Workup

  1. customThe vial was sealed
  2. customThe mixture was evaporated under reduced pressure
  3. customthe residue was purified

Sources & evidence

ORD record
ord-7509163a7b3c479aad8bc31ed50e19cb
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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