Sodium Bicarbonate → HCID 69289151, compound

HRID 899082Notes

Reaction equation

HRID 899082 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][Mg]Br.[CH2:12]([N:19]1[CH2:24][CH2:23][O:22][CH:21]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)=[O:26])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>O1CCCC1>[CH2:12]([N:19]1[CH2:24][CH2:23][O:22][CH:21]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)([OH:26])[CH2:5][C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 59693648HCID 59693648, compoundHCID 178489471HCID 178489471, compound2×

Product 1

HCID 69289151HCID 69289151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A magnetically stirred 0.25M tetrahydrofuran solution of commercially available 2-methoxybenzylmagnesium bromide (available from Rieke-Metals) (80 ml, 3 equiv.) under nitrogen atmosphere was cooled to −10° C. and to this was added neat (4-Benzyl-morpholin-2-yl)-1-(3-fluoro-phenyl)-methanone (2.1 g, 1 equiv.). The solution was allowed to warm to room temperature and reaction progress followed using mass spectrometry. After 1.5 hours 2-methoxybenzylmagnesium bromide solution (14 ml, 0.5 equiv.) was again added to the reaction and after a further 0.5 hours an aqueous saturated solution of NaHCO3 (50 mL) was added to halt the reaction. The aqueous solution was extracted with diethyl ether, the organic phase dried with MgSO4, evaporated in vacuo to give 2.8 g of a yellow amorphous solid. The compound was taken without further purification in the next step. LCMS (6 minutes method) [M+H]+=422 @ Rt 3.03 and 2.86 min. major peaks.

Workup

  1. customreaction progress
  2. additionwas added
  3. customthe reaction
  4. extractionThe aqueous solution was extracted with diethyl ether
  5. dry with materialthe organic phase dried with MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-39ecfd4d20fd4c558cc63d3c86ae8384
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

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