Potassium Carbonate → HCID 22051052, compound

HRID 1866984Notes

Reaction equation

HRID 1866984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]1=[O:16].[Br:22]N1C(=O)CCC1=O.[F:30][C:31]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:32]=1[CH2:33]Br.C(=O)([O-])[O-].[K+].[K+]>>[Br:22][C:10]1[C:9](=[O:16])[N:8]([C:7]2[C:6]([Cl:17])=[CH:5][C:4]([S:18]([NH2:21])(=[O:19])=[O:20])=[CH:3][C:2]=2[Cl:1])[C:13]([CH3:14])=[CH:12][C:11]=1[O:15][CH2:33][C:32]1[CH:35]=[CH:36][C:37]([F:39])=[CH:38][C:31]=1[F:30]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724220HCID 54724220, compound

Product 1

HCID 22051052HCID 22051052, compoundYield 16.2%

Procedure

A mixture of 3,5-dichloro-4-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)benzenesulfonamide (0.18 g, 0.0005 mol), N-bromosuccinimide (0.1 g, 0.00056 mol)in acetici acid (2.0 mL) was stirred at room temperature under argon atmosphere for 1 h. Acetic acid was removed in vacuo, the residue was dissolved in DMF (2.0 mL), and added 2,4-difluorobenzyl bromide (0.128 g, 0.0006 mol), potassium carbonate (0.1 g, 0.0007 mol). The resulting mixture was stirred at room temperature for 1 h. The solvents were distilled in vacuo, and the residue was purified by flash chromatography (EtOAc/hexane 1:3 v/v) to give 0.14 g of partially purified product. This was further purified by reverse-phase HPLC using 10-90% CH3CN/Water (30 min gradient) at a flow rate of 100 mL/min. The appropriate fractions (m/z 553) were combined and freeze dried to afford 0.045 g of pale yellow powder. This was partitioned between EtOAc (25 ml) and 5% sod. bicarbonate. The organic phase was washed with water, dried (Na2SO4) and concentrated under reduced pressure. This material was dried invacuo to afford the title compound (0.033 g) as a white amorphous substance:

Workup

  1. customAcetic acid was removed in vacuo
  2. dissolutionthe residue was dissolved in DMF (2.0 mL)
  3. stirringThe resulting mixture was stirred at room temperature for 1 h
  4. distillationThe solvents were distilled in vacuo
  5. customthe residue was purified by flash chromatography (EtOAc/hexane 1:3 v/v)
  6. customto give 0.14 g of partially purified product
  7. customThis was further purified by reverse-phase
  8. custom10-90% CH3CN/Water (30 min gradient)
  9. customfreeze dried

Sources & evidence

ORD record
ord-88e33946511a442cbb3203cb4d0e6bdd
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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