Sodium Carbonate → HCID 46913617, compound

HRID 1025394Notes

Reaction equation

HRID 1025394 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.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)O1.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:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)=[CH:3][C:4]3=[N:10][CH:9]=2)=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86663322HCID 86663322, compound

Product 1

HCID 46913617HCID 46913617, compoundYield 51.7%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a 5 mL microwave tube was added N-(5-(7-bromoimidazo[1,2-a]pyridin-3-yl)-2-chloropyridin-3-yl)dimethylaminosulfonamide (0.107 g, 0.248 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.061 g, 0.298 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.018 g, 0.025 mmol), sodium carbonate (0.311 mL, 0.621 mmol), and dioxane (3 mL). The resulting mixture was sealed and heated in a microwave at 110° C. for 20 min. Solvent was removed and the residue was partitioned between pH 7-buffer (1M TRIS-HCL) and DCM. The aqueous layer was extracted with DCM (2×15 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude material was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-340, 40 g SiO2, DCM:MeOH=97%:3% Flow=40 mL/min) to afford the desired product as light brown solid (55.0 mg). MS (EI, pos.) calcd for C19H17ClN6O2S: 428.1; found: 428.9.

Workup

  1. customThe resulting mixture was sealed
  2. customSolvent was removed
  3. customthe residue was partitioned between pH 7-buffer (1M TRIS-HCL) and DCM
  4. extractionThe aqueous layer was extracted with DCM (2×15 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude material was purified

Sources & evidence

ORD record
ord-b4ab744a6c8b4547a539b14bd650de06
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

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