Lithium Bromide → HCID 9900530, compound

HRID 396384Notes

Reaction equation

HRID 396384 reaction equation
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:5].[Li][CH3:25].[Li+].[Br-]>C1COCC1>[C:11]1([C:9]2[S:10][C:6]([C:4](=[O:5])[CH3:25])=[C:7]([N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[N:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 82050Lithium BromideHCID 21354781HCID 21354781, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 9900530HCID 9900530, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above-prepared 2-phenyl-4-piperidin-1-yl-thiazole-5-carboxylic acid methoxy-methyl-amide (0.754 mmol) in THF (5 mL) was added at 0° C. MeLi.LiBr (0.83 mmol). The reaction mixture was stirred until the reaction was complete, then quenched by the addition of saturated ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to give a brown oil. Silica gel chromatography provided the title compound (72%) as a yellowish oil. 1H NMR (CDCl3): δ 1.6-1.8 (m, 6H), 2.45 (s, 3H), 3.5 (m, 4H), 7.4-7.5 (m, 3H), 8.0 (m, 2H).

Workup

  1. customquenched by the addition of saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil

Sources & evidence

ORD record
ord-5335d778b31849d587f256349ea23706
Source dataset
uspto-grants-2003_08
Patent number
US06608087B1

Reaction notes

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