Potassium Carbonate → HCID 52932050, compound

HRID 877353Notes

Reaction equation

HRID 877353 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:22]2[N:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH2:28](B(O)O)[CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.[Ag-]=O>[CH:18]1([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][C:10]([NH:9][C@H:8]([C:22]3[N:23]=[N:24][N:25]([CH3:27])[CH:26]=3)[C:5]3[CH:6]=[CH:7][C:2]([CH2:28][CH2:29][CH3:30])=[CH:3][CH:4]=3)=[O:21])=[CH:13][CH:14]=2)[CH2:20][CH2:19]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 3510651-Propylboronic acidHCID 52932049HCID 52932049, compound

Product 1

HCID 52932050HCID 52932050, compoundYield 30.6%

Reagents, catalysts & solvents 4

HCID 178418778HCID 178418778, compoundCatalystHCID 178418807HCID 178418807, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.086 g (0.202 mmol) N-[(S)-(4-bromophenyl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-cyclopropylphenyl)acetamide in 1.0 ml THF was added 0.021 g (0.243 mmol) n-propylboronic acid, 0.017 g (0.020 mmol) PdCl2(dppf)-CH2Cl2 adduct, 0.084 g (0.607 mmol) solid potassium carbonate, and 0.117 g (0.607 mmol) Silver(I) oxide. The reaction mixture was irradiated in the microwave at 150° C. for 30 mins. The resulting solution was diluted with CH2Cl2, washed twice with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) to afford 0.024 g (30.6%) 2-(4-cyclopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(4-propylphenyl)methyl]acetamide. 1H NMR (CDCl3, 400 MHz) 7.25 (m, 1H); 7.17-7.02 (m, 8H); 6.68 (d, J=8.24 Hz, 1H); 6.25 (d, J=7.78 Hz, 1H); 4.03 (s, 3H); 3.56 (s, 2H); 2.54 (t, J=7.42 Hz, 2H); 1.90-1.84 (m, 1H); 1.65-1.55-(m, 2H); 0.97-0.90 (m, 5H); 0.69-0.65 (m, 2H). HRMS (ES) [M+1]+ calcd for C24H28N4O: 389.2341. Found: 389.2343.

Workup

  1. customThe reaction mixture was irradiated in the microwave at 150° C. for 30 mins
  2. washwashed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. additionby preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18)

Sources & evidence

ORD record
ord-c17863fbff394141a202ef50038d6f43
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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