Sodium Carbonate → Methyl 4-(3-((4-(trifluoromethoxy)phenyl)carbamoyl)phenyl)thiophene-2-carboxylate

HRID 629055Notes

Reaction equation

HRID 629055 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[S:33][CH:34]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>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.O>[F:16][C:15]([F:18])([F:17])[O:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5]([C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[S:33][CH:34]=3)[CH:21]=[CH:20][CH:19]=2)=[O:6])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 13710333-bromo-N-(4-(trifluoromethoxy)phenyl)benzamideHCID 52911233Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate

Product 1

HCID 72202880Methyl 4-(3-((4-(trifluoromethoxy)phenyl)carbamoyl)phenyl)thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-bromo-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 3.1, 50 mg, 0.139 mmol in 2.4 mL DME), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (0.180 mmol), 2 M Na2CO3 (0.104 mL, 0.208 mmol), water (0.8 mL), and (Ph3P)4Pd (8 mg, 6.94 μmol) in a sealed vial were subjected to MW irradiation at 150° C. for 10 min. The RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL), the cartridge was washed with MeOH (10 mL) and the combined filtrates were evaporated to dryness under reduced pressure to give the crude product was purified by preparative HPLC to afford the title compound. UPLC-MS (Condition 6) tR=2.37 min, m/z=422.3 [M+H]+.

Workup

  1. customvial were subjected to MW irradiation at 150° C. for 10 min
  2. filtrationThe RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL)
  3. washthe cartridge was washed with MeOH (10 mL)
  4. customthe combined filtrates were evaporated to dryness under reduced pressure
  5. customto give the crude product
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-34af188d1f53429d9692372f75369aff
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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