Sodium Carbonate → HCID 118483220, compound

HRID 1773354Notes

Reaction equation

HRID 1773354 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH3:31])[C:16](=[O:30])[C:17](Cl)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([F:28])[CH:21]=3)[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O:33]1[C:37]2[CH:38]=[CH:39][C:40](B(O)O)=[CH:41][C:36]=2[CH:35]=[CH:34]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[C:1]([O:5][C:6](=[O:32])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH3:31])[C:16](=[O:30])[C:17]([C:40]3[CH:41]=[CH:36][C:35]4[C:39]=3[CH:38]=[CH:37][O:33][CH:34]=4)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([F:28])[CH:21]=3)[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 4197999(1-Benzofuran-5-yl)boronic acidHCID 118483182HCID 118483182, compound

Product 1

HCID 118483220HCID 118483220, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of {1-[5-chloro-4-(4-cyano-3-fluoro-phenyl)-1-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester (200 mg, 0.45 mmol), benzofuran-5-boronic acid (120 mg, 0.68 mmol), Pd(PPh3)4 (26 mg, 0.05 mmol) and 2M Na2CO3 (0.9 mL) in 1,4-dioxane (200 mL) was refluxed overnight under N2 atmosphere. The reaction mixture was diluted with water and extracted with EA (3×). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica chromatography to give 100 mg of the title product (42%). [M+H] Calc'd for C30H30FN5O4, 543. Found, 543.

Workup

  1. temperaturewas refluxed overnight under N2 atmosphere
  2. extractionextracted with EA (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-6d47213a35af4ebca4ae5ace895ea538
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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