Dichloromethane → HCID 59302970, compound

HRID 1692141Notes

Reaction equation

HRID 1692141 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19](F)[C:18](Cl)=[CH:17][C:16]=2[C:23]2[N:27]([CH3:28])[C:26]([CH2:29][CH3:30])=[N:25][N:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.C(N(CC)CC)C.CN([CH:44]=[O:45])C.[CH3:46][OH:47]>>[CH3:46][O:47][C:44](=[O:45])[C:18]1[CH:19]=[CH:20][C:15]([NH:14][S:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:10][CH:9]=2)(=[O:12])=[O:13])=[C:16]([C:23]2[N:27]([CH3:28])[C:26]([CH2:29][CH3:30])=[N:25][N:24]=2)[CH:17]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 21901440N,N-dimethylformamide methanolHCID 24996716HCID 24996716, compound

Product 1

HCID 59302970HCID 59302970, compound

Conditions

Temperature
80 °C

Procedure

A 15 mL pressure vessel was charged with 4-tert-butyl-N-[4-iodo-2-(5-ethyl-4-methyl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide (prepared according to general procedure C, 551 mg, 1.05 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (1:1) (86 mg, 0.105 mmol), triethylamine (290 μL, 2.1 mmol), and DMF/MeOH (4:1) (5 mL). The vessel was placed under an atmosphere of CO (50 p.s.i.), heated to 80° C., and stirred overnight. The following day, the volatiles were removed in vacuo, the residue dissolved in EtOAc, and the organics washed twice with 1 M HCl. The aqueous solution was then extracted three times with EtOAc. The EtOAc extractions were then pooled together and washed with brine. The organic solvent was then removed and the resultant residue was purified by silica gel chromatography to afford 4-(4-tert-butyl-benzenesulfonylamino)-3-(5-ethyl-4-methyl-4H-[1,2,4]triazol-3-yl)-benzoic acid methyl ester as a yellow foam: MS (ES) M+H expected 457.2, found 457.1.

Workup

  1. customThe following day, the volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washthe organics washed twice with 1 M HCl
  4. extractionThe aqueous solution was then extracted three times with EtOAc
  5. extractionThe EtOAc extractions
  6. washwashed with brine
  7. customThe organic solvent was then removed
  8. customthe resultant residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7bbc1af93a7e4e4abd06d5fe7fec9769
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

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