Diethyl Ether → HCID 68698151, compound

HRID 644028Notes

Reaction equation

HRID 644028 reaction equation
C(OC([C:6]1[S:10][N:9]=[C:8]([C:11]2[C:19]3[C:14](=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:12]=2)[N:7]=1)=O)C.C[Mg]Br.[CH2:32]([O:34]CC)[CH3:33]>>[CH:23]1([CH2:22][N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[C:11]([C:8]3[N:7]=[C:6]([C:32](=[O:34])[CH3:33])[S:10][N:9]=3)=[CH:12]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 68697255HCID 68697255, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 68698151HCID 68698151, compound

Procedure

To a cooled solution (dry-ice acetone bath) of 3-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester (500 mg, 1.3 mmol) in diethyl ether (50 ml) was added methyl magnesium bromide solution (0.52 ml, 3M in diethyl ether, 1.56 mmol) and the reaction stirred for 15 minutes, a further portion of methyl magnesium bromide solution (0.25 ml, 3M in diethyl ether, 0.75 mmol) was then added and the reaction mixture stirred for 5 minutes. The reaction was then quenched with saturated aqueous ammonium chloride (5 ml) and the reaction allowed to warm to room temperature. The reaction mixture was poured into a separating funnel and the organics washed with water (20 ml). The aqueous layer was then backwashed with diethyl ether (20 ml). The combined organic layers were dried over magnesium sulfate, filtered and the solvent removed in vacuo. The resulting residue was purified by flash column chromatography to give 1-[3-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-[1,2,4]thiadiazol-5-yl]-ethanone (170 mg, 0.46 mmol) as a yellow solid.

Workup

  1. stirringthe reaction mixture stirred for 5 minutes
  2. customThe reaction was then quenched with saturated aqueous ammonium chloride (5 ml)
  3. additionThe reaction mixture was poured into a separating funnel
  4. washthe organics washed with water (20 ml)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ec21dce4effd46938f9117ed38b7cf7b
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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