Potassium Carbonate → N-(6-(3-carbamoyl-4-methoxyphenyl)naphthalen-2-yl)thiophene-3-carboxamide

HRID 908307Notes

Reaction equation

HRID 908307 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([NH:31][C:32]([C:34]2[CH:38]=[CH:37][S:36][CH:35]=2)=[O:33])[CH:25]=[CH:24]3)O1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>[Pd].O>[C:7]([C:6]1[CH:10]=[C:2]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([NH:31][C:32]([C:34]2[CH:38]=[CH:37][S:36][CH:35]=2)=[O:33])[CH:25]=[CH:24]3)[CH:3]=[CH:4][C:5]=1[O:11][CH3:12])(=[O:8])[NH2:9]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 230551875-Iodo-2-methoxybenzamideHCID 67386422N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide

Product 1

HCID 58828842N-(6-(3-carbamoyl-4-methoxyphenyl)naphthalen-2-yl)thiophene-3-carboxamideYield 15.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

5-iodo-2-methoxybenzamide (47.9 mg, 0.173 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (140.4 mg, 0.370 mmol), Fibercat palladium catalyst (Johnson-Matthey, 70.1 mg), and K2CO3 (2 M in water, 0.65 ml, 1.3 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (1.8 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 60 Watts and 85 C for 20 minutes. The reaction was then cooled to room temperature, diluted with water (5 ml), and extracted with EtOAc (4×10 ml). The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified via silica gel (Biotage instrument, 13%->100% EtOAc/hexanes). This crude material was then purified via HPLC (10%->95% MeCN/water with 0.1% TFA) to afford title compound (10.6 mg, 15%). MS (ESI pos. ion) m/z: 403 (M+H). Calc'd Exact Mass for C23H18N2O3S: 402.

Workup

  1. additionwas added
  2. customThe reaction tube was sealed
  3. temperatureheated in the microwave (CEM microwave) at 60 Watts and 85 C for 20 minutes
  4. extractionextracted with EtOAc (4×10 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via silica gel (Biotage instrument, 13%->100% EtOAc/hexanes)
  9. customThis crude material was then purified via HPLC (10%->95% MeCN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-7c65003a4c1d4632a6832eacc017e23d
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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