Sodium Carbonate → HCID 46913527, compound

HRID 1025393Notes

Reaction equation

HRID 1025393 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([NH:18][S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[C:14]([Cl:17])=[N:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.Br[C:26]1[CH:27]=[C:28](NS(N(C)C)(=O)=O)[C:29](Cl)=[N:30][CH:31]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].BrC1C=CN2C(I)=CN=C2C=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[Cl:17][C:14]1[C:13]([NH:18][S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])=[CH:12][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([C:27]4[CH:26]=[CH:31][N:30]=[CH:29][CH:28]=4)=[CH:3][C:4]3=[N:10][CH:9]=2)=[CH:16][N:15]=1

Participants

9

Reactant 6

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 59519509HCID 59519509, compoundHCID 666714367-BroMo-3-iodo-iMidazo[1,2-a]pyridineHCID 86663322HCID 86663322, compound

Product 1

HCID 46913527HCID 46913527, compound

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

N-(5-(7-bromoimidazo[1,2-a]pyridin-3-yl)-2-chloropyridin-3-yl)dimethylaminosulfonamide. To a 100 mL round bottom flask was added N-(5-bromo-2-chloropyridin-3-yl)dimethylaminosulfonamide (0.220 g, 0.699 mmol), Bis(pinacolato)diboron (0.266 g, 1.049 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.051 g, 0.070 mmol), potassium acetate (0.069 g, 0.699 mmol) and dioxane (20 mL). The resulting mixture was heated at 95° C. under N2 for 4 h. The reaction mixture was removed from the hot plate followed by the addition of 7-bromo-3-iodoimidazo[1,2-a]pyridine (0.226 g, 0.699 mmol), sodium carbonate (0.874 mL, 1.748 mmol), and 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.051 g, 0.070 mmol). The resulting mixture was then reheated at 95° C. under N2 for 20 h. The reaction was cooled to rt. The solvent was removed. The residue was partitioned between pH 7-buffer (1M TRIS-HCL) and CHCl3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 40 g SiO2, DCM:EtOAc:MeOH (2M NH3)=80%:17%:3%, Flow=40 mL/min) to afford the desired product as brown foam-like solid (50.0 mg). MS (ESI pos. ion) m/z: 429.8. Calcd exact mass for C14H13BrClN5O2S: 428.9. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.91 (s, 6H) 6.88 (br. s., 1H) 7.04 (d, J=7.89 Hz, 1H) 7.78 (s, 1H) 7.93 (s, 1H) 8.08 (s, 1H) 8.16 (d, J=7.16 Hz, 1H) 8.34 (s, 1H).

Workup

  1. customThe reaction mixture was removed from the hot plate
  2. temperatureThe reaction was cooled to rt
  3. customThe solvent was removed
  4. customThe residue was partitioned between pH 7-buffer (1M TRIS-HCL) and CHCl3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-91de25c1adff485abae988bc8d9a2faa
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

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