Toluene → HCID 66774514, compound

HRID 1644845Notes

Reaction equation

HRID 1644845 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[C:7](B(O)O)[CH:6]=1)[CH:2]([CH3:4])[CH3:3].Br[C:22]1[CH:33]=[CH:32][C:25]([CH2:26][N:27]2[CH:31]=[N:30][N:29]=[N:28]2)=[CH:24][CH:23]=1.C1(C)C=CC=CC=1.[OH-].[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[C:7]([C:22]2[CH:33]=[CH:32][C:25]([CH2:26][N:27]3[CH:31]=[N:30][N:29]=[N:28]3)=[CH:24][CH:23]=2)[CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 23404119HCID 23404119, compound

Product 1

HCID 66774514HCID 66774514, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-iso-Butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (401.0 mg, 1.256 mmol, see Example 1(c) above), 1-(4-bromobenzyl)-1H-tetrazole (199.4 mg, 0.834 mmol, see step (a) above), toluene (20 mL), ethanol (3.0 mL), NaOH (1.0M, 5.0 mL, 5.0 mmol) and Pd(PPh3)4 (29.0 mg, 0.25 mmol) were mixed under N2. The mixture was warmed to reflux for 2 hours. The mixture was diluted with EtOAc (20 mL), washed with water and brine, and dried over MgSO4. The solvent was removed and the residue was separated by column chromatography using CHCl3:MeOH (40:1) as eluent to give 222.4 mg of the sub-title compound (yield: 62%).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 2 hours
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed
  6. customthe residue was separated by column chromatography

Sources & evidence

ORD record
ord-e7c0d5dedd604b669874135b8bf1d8ef
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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