Sodium Bicarbonate → HCID 118045711, compound

HRID 596056Notes

Reaction equation

HRID 596056 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:3][CH2:2]1.Cl[C:24]1[CH:33]=[C:32]([F:34])[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([C:35]#[N:36])[CH:25]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])(O)=O.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCOC(C)=O.O.COCCOC>[NH2:13][C:10]1[C:9]([C:24]2[CH:33]=[C:32]([F:34])[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([C:35]#[N:36])[CH:25]=2)=[CH:8][C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:12][N:11]=1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 118045619HCID 118045619, compoundHCID 123469022HCID 123469022, compound

Product 1

HCID 118045711HCID 118045711, compoundYield 36.5%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a 2 mL microwave vial were added 5-(tetrahydro-2H-pyran-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (638 mg, 1.049 mmol), methyl 4-chloro-2-cyano-6-fluorobenzoate (140 mg, 0.655 mmol), Pd2(dba)3 (30.0 mg, 0.033 mmol), XPhos (31.2 mg, 0.066 mmol), NaHCO3 (275 mg, 3.28 mmol), DME (3 mL) and H2O (1.5 mL). The solution was heated under microwave at 100° C. for 15 min. Water and EtOAc were added and the aqueous layer was extracted three times with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated. The residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:4) to give the product as a yellow foam (85 mg). LCMS (m/z) 356.1 (MH+), 0.58 min.

Workup

  1. extractionthe aqueous layer was extracted three times with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:4)

Sources & evidence

ORD record
ord-ff276853d45c4c02b7dd9125f4103239
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…