Sodium Bicarbonate → HCID 18614746, compound

HRID 1265187Notes

Reaction equation

HRID 1265187 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]2[C:18](=[O:23])[C:19]([F:22])([F:21])[CH2:20][C:15]2=[N:14]1.[CH3:24][Mg]Br.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]2[C:18]([CH3:24])([OH:23])[C:19]([F:22])([F:21])[CH2:20][C:15]2=[N:14]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18614760HCID 18614760, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18614746HCID 18614746, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (91) (3.6 mg, 9.7 mmol) in 300 mL THF was added methyl magnesium bromide (50 mL, 3.0 M) at 0° C. The solution was then stirred at room temperature for 30 min. The mixture was poured into 5 mL of saturated NaHCO3 solution and extracted with dichlormethane (5 mL×3). The organic layers were combined, washed with brine, and dried with anhydrous sodium sulfate. The mixture was then chromatographed on a silica gel TLC plate using hexane/ethyl acetate (3:1) to give (93): yield 98%; 1H NMR (400 MHz, CDCl3) δ 7.73 (s, 2H), 7.47 (s, 1H), 3.65-3.31 (m, 2H), 2.46 (br s, 1H), 1.67 (s, 3H).

Workup

  1. extractionextracted with dichlormethane (5 mL×3)
  2. washwashed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe mixture was then chromatographed on a silica gel TLC plate

Sources & evidence

ORD record
ord-cd5321688ba648c98ed612200f78ca14
Source dataset
uspto-grants-2003_04
Patent number
US06545033B1

Reaction notes

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