Potassium Carbonate → HCID 22051052, compound

HRID 1831984Notes

Reaction equation

HRID 1831984 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-ed9f1d2143844ea2873028bea4e8ca2a
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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