Potassium Carbonate → 1-(Cyclohexylmethyl)-N-cyclopropyl-5-(3,5-di-tert-butylphenyl)-2-methyl-1H-pyrrole-3-sulfonamide

HRID 1844711Notes

Reaction equation

HRID 1844711 reaction equation
Br[C:2]1[N:6]([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C:5]([CH3:14])=[C:4]([S:15]([NH:18][CH:19]2[CH2:21][CH2:20]2)(=[O:17])=[O:16])[CH:3]=1.[C:22]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:31]=1)([CH3:25])([CH3:24])[CH3:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:8]1([CH2:7][N:6]2[C:2]([C:28]3[CH:27]=[C:26]([C:22]([CH3:24])([CH3:23])[CH3:25])[CH:31]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:29]=3)=[CH:3][C:4]([S:15]([NH:18][CH:19]3[CH2:21][CH2:20]3)(=[O:17])=[O:16])=[C:5]2[CH3:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11470330(3,5-Di-tert-butylphenyl)boronic acidHCID 708691515-Bromo-1-(cyclohexylmethyl)-N-cyclopropyl-2-methyl-1H-pyrrole-3-sulfonamide

Product 1

HCID 708690921-(Cyclohexylmethyl)-N-cyclopropyl-5-(3,5-di-tert-butylphenyl)-2-methyl-1H-pyrrole-3-sulfonamideYield 10%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

The solution of compound 3d (600 mg, 1.60 mmol), (3,5-di-tert-butylphenyl)boronic acid (700 mg, 3.00 mmol), Pd(dppf)Cl2 (80 mg) and K2CO3 (483 mg, 3.50 mmol) in DMF (30 mL) was heated at 120° C. under N2 for 16 h. The resulting solution was concentrated, diluted with water and extracted with EA twice. The combined organic layers were washed with water (3×) and brine (3×) consecutively, dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=10/1) to give compound 3 (70 mg, 10%) as a white solid. 1H-NMR (300 MHz, CDCl3) δ: 0.58-0.66 (m, 6H), 0.95-1.00 (m, 3H), 1.34 (s, 18H), 1.30-1.35 (m, 3H), 1.40-1.55 (m, 3H), 2.32-2.35 (m, 1H), 2.54 (s, 3H), 3.73 (d, J=7.2 Hz, 2H), 4.69 (s, 11-1), 6.44 (s, 1H), 7.15 (s, 2H), 7.40 (s, 1H). MS Calcd.: 484; MS Found: 485 (M+1).

Workup

  1. concentrationThe resulting solution was concentrated
  2. additiondiluted with water
  3. extractionextracted with EA twice
  4. washThe combined organic layers were washed with water (3×) and brine (3×) consecutively
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CC (PE/EA=10/1)

Sources & evidence

ORD record
ord-9500d100b62b48b89a5aec92170763c0
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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