Sodium Carbonate → HCID 118195352, compound

HRID 923916Notes

Reaction equation

HRID 923916 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([NH:27]C(=O)OC(C)(C)C)[CH2:23]2)=[N:4][CH:5]=[C:6]([C:8](=[O:21])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH:7]=1.[N:35]1[CH:40]=[C:39](B(O)O)[CH:38]=[N:37][CH:36]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[NH2:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:39]3[CH:40]=[N:35][CH:36]=[N:37][CH:38]=3)=[CH:7][C:6]([C:8]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:20])[F:19])=[CH:14][CH:15]=3)=[O:21])=[CH:5][N:4]=2)[CH2:23]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 118198934HCID 118198934, compound

Product 1

HCID 118195352HCID 118195352, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (R)-tert-butyl (1-(3-bromo-5-((4-(trifluoromethoxy)phenyl)carbamoyl)pyridin-2-yl)pyrrolidin-3-yl)carbamate (Stage 93.1, 60 mg, 0.110 mmol), pyrimidin-5-ylboronic acid (21 mg, 0.164 mmol), 2M Na2CO3 (0.2 mL, 0.4 mmol) and DME (4 mL) was flushed with argon. PdCl2(dppf)(CH2Cl2) (10 mg, 0.012 mmol) was added and the mixture was subjected to MW irradiation 140° C. for 30 min. The RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL), the cartridge was washed with MeOH and the solvent was evaporated off under reduced pressure to give a residue which was purified by preparative LC-MS to afford the title compound. LC-MS (Condition 6) tR=0.88 min, m/z=445.0 [M+H]+.

Workup

  1. customwas flushed with argon
  2. customthe mixture was subjected to MW irradiation 140° C. for 30 min
  3. filtrationThe RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL)
  4. washthe cartridge was washed with MeOH
  5. customthe solvent was evaporated off under reduced pressure
  6. customto give a residue which
  7. customwas purified by preparative LC-MS

Sources & evidence

ORD record
ord-1367562683924380b8eba700f32e5882
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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