Sodium Bicarbonate → HCID 18614763, compound

HRID 1265185Notes

Reaction equation

HRID 1265185 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])[CH:19]([F:22])[CH:20]([F:21])[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:10])([F:11])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]2[C:18]([CH3:24])([OH:23])[CH:19]([F:22])[CH:20]([F:21])[C:15]2=[N:14]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18614742HCID 18614742, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18614763HCID 18614763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (87) (6.6 mg, 17.8 mmol) in 500 mL THF was added methyl magnesium bromide (10 mL, 3.0 M). The mixture was stirred at room temperature for 3 h. The mixture was poured into 5 mL dilute NaHCO3 solution. The aqueous solution was extracted with dichloromethane (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 dichloromethane/ethyl acetate (9:1) to give (88): yield (32%): 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 2H), 7.57 (s, 1H), 5.89 (dd, 1H, J=4.25, 56.66 Hz), 4.92 (ddd, 1H, J=4.25, 15.76, 48.17 Hz), 2.47 (br s, 1H), 1.75 (s, 3H).

Workup

  1. extractionThe aqueous solution was extracted with dichloromethane (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-715767317d644d928187c525ea021d34
Source dataset
uspto-grants-2003_04
Patent number
US06545033B1

Reaction notes

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