Potassium Carbonate → N-(6-(5-carbamoyl-2-methylphenyl)naphthalen-2-yl)thiophene-3-carboxamide

HRID 908295Notes

Reaction equation

HRID 908295 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH2:7])=[O:6].CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([NH:30][C:31]([C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)=[O:32])[CH:24]=[CH:23]3)O1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>[Pd].O>[C:5]([C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([NH:30][C:31]([C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)=[O:32])[CH:24]=[CH:23]3)[CH:3]=1)(=[O:6])[NH2:7]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 6810613-Bromo-4-methylbenzamideHCID 67386422N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide

Product 1

HCID 58828866N-(6-(5-carbamoyl-2-methylphenyl)naphthalen-2-yl)thiophene-3-carboxamideYield 8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

3-bromo-4-methylbenzamide (22.7 mg, 0.106 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (62.5 mg, 0.165 mmol), Fibercat palladium catalyst (Johnson-Matthey, 35.1 mg), and K2CO3 (2 M in water, 0.24 ml, 0.48 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (1.1 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 60 Watts and 80 C for 10 minutes and then for 20 minutes. The reaction was cooled to room temperature, diluted with water (5 ml), extracted with dichloromethane (3×10 ml), diluted with 1,4-dioxane (10 ml), and extracted with EtOAc (3×10 ml). The organic extracts were combined, dried over magnesium sulfate, filtered, concentrated, and purified on HPLC (10%->95% MeCN/water with 0.1% TFA) to afford title compound (3.2 mg, 8%). MS (ESI pos. ion) m/z: 387 (M+H). Calc'd Exact Mass for C23H18N2O2S: 386.

Workup

  1. additionwas added
  2. customThe reaction tube was sealed
  3. temperatureheated in the microwave (CEM microwave) at 60 Watts and 80 C for 10 minutes
  4. extractionextracted with dichloromethane (3×10 ml)
  5. additiondiluted with 1,4-dioxane (10 ml)
  6. extractionextracted with EtOAc (3×10 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on HPLC (10%->95% MeCN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-4544e62d200e465bab08f43cc754832b
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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