Sodium Carbonate → HCID 58127161, compound

HRID 1623259Notes

Reaction equation

HRID 1623259 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([NH:14][CH2:15][C:16]2([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:8]=1)(=O)=O.[Cl:26][C:27]1[C:28](B(O)O)=[CH:29][C:30]([F:33])=[N:31][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:26][C:27]1[C:28]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([NH:14][CH2:15][C:16]3([C:22]#[N:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[N:8]=2)=[CH:29][C:30]([F:33])=[N:31][CH:32]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 44754822(5-Chloro-2-fluoropyridin-4-yl)boronic acidHCID 58127223HCID 58127223, compound

Product 1

HCID 58127161HCID 58127161, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-fluoro-6-((4-cyano-tetrahydro-2H-pyran-4-yl)methylamino)pyridin-2-yl trifluoromethanesulfonate (200 mg, 0.522 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (183.2 mg, 1.044 mmol), PdCl2(dppf)-CH2Cl2 adduct (85.1 mg, 0.104 mmol), and SODIUM CARBONATE (221.6 mg, 2.08 mmol, in 1 ml of water) in DME (3 ml) was de-gassed and heated at 110° C. for 20 min in a sealed microwave vial, cooled. The upper layer of mixture was separated, the bottom one was extracted with ethyl acetates, the organic layers were combined and concentrated to afford the crude product, which was purified by ISCO (10 to 50% ethyl acetate in heptane, 20 min) to afford 150 mg (79% yield) of the desired product was an off-white solid. LCMS (m/z): 365.1 [M+H]+; retention time=0.929 min.

Workup

  1. customwas de-gassed
  2. temperaturecooled
  3. customThe upper layer of mixture was separated
  4. extractionthe bottom one was extracted with ethyl acetates
  5. concentrationconcentrated
  6. customto afford the crude product, which
  7. customwas purified by ISCO (10 to 50% ethyl acetate in heptane, 20 min)

Sources & evidence

ORD record
ord-639dd5dfb49f4d52acfbf7de35817218
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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