Sodium Hydroxide → HCID 66775751, compound

HRID 1644848Notes

Reaction equation

HRID 1644848 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][CH:29]=[N:28]2)=[CH:24][CH:23]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:27]1([CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:7]3[CH:6]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[S:9][C:8]=3[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[CH:33][CH:32]=2)[CH:31]=[N:30][CH:29]=[N:28]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 19043019HCID 19043019, compound

Product 1

HCID 66775751HCID 66775751, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
80 °C

Procedure

5-iso-Butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (0.479 g, 1.5 mmol, see Example 1(c) above), 1-(4-bromobenzyl)-1H-[1,2,4]triazole (0.238 g, 1 mmol, see step (a) above), Pd(OAc)2 (15.7 mg, 0.03 mmol), triphenyl phosphine (15.7 mg, 0.06 mmol) and NaOH (0.16 g, 4 mmol) were dissolved in 4 mL of toluene/ethanol (4:1) in a thick walled glass tube, and were then heated to 80° C. for 1 h. The reaction mixture was cooled to rt, extracted with ethyl acetate and water and subsequently dried over K2CO3. The solvent was evaporated and the reaction mixture was separated on a silica column (dichloromethane+1% methanol to dichloromethane+4% methanol) to yield 0.288 g of the sub-title compound (65% yield).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with ethyl acetate and water
  3. dry with materialsubsequently dried over K2CO3
  4. customThe solvent was evaporated
  5. customthe reaction mixture was separated on a silica column (dichloromethane+1% methanol to dichloromethane+4% methanol)

Sources & evidence

ORD record
ord-cba9a1596d27426a9525a18b2923a596
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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