Sodium Carbonate → HCID 58988132, compound

HRID 2234977Notes

Reaction equation

HRID 2234977 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([Cl:18])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:19][C:20]1[O:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([C:23]3[O:24][C:20]([CH3:19])=[CH:21][CH:22]=3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343725-Methyl-2-furanboronic AcidHCID 589881394-Bromo-N-(2-chloro-4-pyridinyl)benzenesulfonamide

Product 1

HCID 58988132HCID 58988132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-chloro-N-(2-chloro-4-pyridinyl)benzenesulfonamide (D3) (350 mg, 1 mmol), 5-methylfuran-2-boronic acid (150 mg, 1.2 mmol), sodium carbonate (230 mg, 2.2 mmol) and dichlorobis(triphenylphosphine) palladium(0) (20 mg, 15 mol %) in 1,2-dimethoxyethane (3 ml) and water (1 ml) was microwaved at 120° C. for 20 min. The reaction mixture was partitioned between ethyl acetate (5 ml) and water (5 ml) and the organic phase was dried and evaporated. Purification by column chromatography eluting with 5-50% ethyl acetate in hexanes afforded the title compound (D4), MS (ES+) m/e 349, 351 [M+H]+.

Workup

  1. customwas microwaved at 120° C. for 20 min
  2. customThe reaction mixture was partitioned between ethyl acetate (5 ml) and water (5 ml)
  3. customthe organic phase was dried
  4. customevaporated
  5. customPurification by column chromatography
  6. washeluting with 5-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f8179ea14eb942f08efb874c61ce3dcb
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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