Sodium Carbonate → HCID 46913618, compound

HRID 1025395Notes

Reaction equation

HRID 1025395 reaction equation
Br[C:2]1[C:3]([CH3:25])=[CH:4][C:5]2[N:6]([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]=2)[CH:7]=1.Br[C:27]1[C:28](C)=[CH:29][C:30]2[N:31](C(I)=CN=2)[CH:32]=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:6]3[CH:7]=[C:2]([C:28]4[CH:27]=[CH:32][N:31]=[CH:30][CH:29]=4)[C:3]([CH3:25])=[CH:4][C:5]3=[N:10][CH:9]=2)=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66677924HCID 66677924, compoundHCID 86663323HCID 86663323, compound

Product 1

HCID 46913618HCID 46913618, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

N-(5-(6-bromo-7-methylimidazo[1,2-a]pyridin-3-yl)-2-chloropyridin-3-yl)dimethylaminosulfonamide. To a 5 mL microwave tube was added N-(2-chloro-5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-yl)-N′,N′-dimethylsulfonamide (0.300 g, 0.830 mmol), 6-bromo-3-iodo-7-methylimidazo[1,2-a]pyridine (0.335 g, 0.995 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(ii) (0.061 g, 0.083 mmol), sodium carbonate (1.037 mL, 2.074 mmol), and dioxane (3 mL). The resulting mixture was sealed and underwent microwave heating at 110° C. for 20 min. The solvent was removed. The residue was partitioned between pH 7-buffer (1M TRIS-HCL) and DCM. The aqueous layer was extracted more with DCM (2×10 mL). The combined organic layer was dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 80 g SiO2, DCM:EtOAc:MeOH=65%:32%:3%, Flow=65 mL/min). The solvent was removed in vacuo to afford the desired product as light yellow solid (160 mg). MS (ESI pos. ion) m/z: 443.8. Calcd exact mass for C15H15BrClN5O2S: 442.9. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.51 (s, 3H) 2.95 (s, 6H) 6.92 (br. s., 1H) 7.59 (s, 1H) 7.75 (s, 1H) 8.09 (s, 1H) 8.34 (s, 1H) 8.48 (s, 1H).

Workup

  1. customThe resulting mixture was sealed
  2. customThe solvent was removed
  3. customThe residue was partitioned between pH 7-buffer (1M TRIS-HCL) and DCM
  4. extractionThe aqueous layer was extracted more with DCM (2×10 mL)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fd1f9aa21b1146f9a7b06d33e1528dd8
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

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