Sodium Carbonate → HCID 10027054, compound

HRID 1782088Notes

Reaction equation

HRID 1782088 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][N:23]3[CH:27]=[C:26]([Cl:28])[N:25]=[N:24]3)[O:19][C:18]2=[O:29])[CH:5]=[CH:6][C:7]=1B1OC(C)(C)C(C)(C)O1.Br[C:31]1[CH:32]=[CH:33][C:34]([C:37]2[N:38]=[N:39][N:40]([CH3:42])[N:41]=2)=[N:35][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][N:23]3[CH:27]=[C:26]([Cl:28])[N:25]=[N:24]3)[O:19][C:18]2=[O:29])[CH:5]=[CH:6][C:7]=1[C:31]1[CH:36]=[N:35][C:34]([C:37]2[N:38]=[N:39][N:40]([CH3:42])[N:41]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 234386535-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridineHCID 57588288HCID 57588288, compound

Product 1

HCID 10027054HCID 10027054, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (5R)-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(4-chloro-1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (300 mg, 0.71 mmol), 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (170 mg, 0.71 mmol), and sodium carbonate (226 mg, 2.13 mmol) in N,N-dimethylformamide:water (5 mL, 10:1) was degassed, flushed with nitrogen, and treated with tetrakis(triphenylphosphine)palladium (0) (82 mg, 10 mol %). The reaction mixture was heated at 70° C. for 3 hours, cooled to room temperature, and evaporated to dryness under reduced pressure. The involatile residue was purified by chromatography on silica gel [elution with dichloromethane:N,N-dimethylformamide (25:1 to 20:1)]. The product fraction was concentrated to a small volume (˜3 mL) and treated with dichloromethane (5 mL) and hexanes (15 mL) to precipitate the product as a colorless amorphous solid (229 mg, 71%).

Workup

  1. customwater (5 mL, 10:1) was degassed
  2. customflushed with nitrogen
  3. additiontreated with tetrakis(triphenylphosphine)palladium (0) (82 mg, 10 mol %)
  4. temperaturecooled to room temperature
  5. customevaporated to dryness under reduced pressure
  6. customThe involatile residue was purified by chromatography on silica gel [elution with dichloromethane:N,N-dimethylformamide (25:1 to 20:1)]
  7. concentrationThe product fraction was concentrated to a small volume (˜3 mL)
  8. additiontreated with dichloromethane (5 mL) and hexanes (15 mL)
  9. customto precipitate the product as a colorless amorphous solid (229 mg, 71%)

Sources & evidence

ORD record
ord-2bd0a83fae8045caac887b4543fd26f6
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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