HCID 86621044, compound → HCID 68856381, compound

HRID 226105Notes

Reaction equation

HRID 226105 reaction equation
CON(C)[C:4]([C:6]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([Br:15])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:18][Mg+].[Br-]>C1COCC1>[Br:15][C:14]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:4](=[O:5])[CH3:18])[C:11]=2[S:12][C:13]=1[CH3:16]

Participants

4

Reactant 2

HCID 86621044HCID 86621044, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 68856381HCID 68856381, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-bromo-2-methyl-benzo[b]thiophene-7-carboxylic acid methoxy-methyl-amide (2.02 g, 6.43 mmol) in THF (65 mL) is cooled to 0° C., treated with CH3MgBr (3.0 M, 2.4 mL, 7.1 mmol). The reaction is stirred at 0° C. for 10 min, then at rt for 10 min. It is cooled to 0° C., quenched with sat. NH4C (10 mL); diluted with H2O (20 mL); treated with 0.1 M HCl (20 mL); extracted with EtOAc (2×40 mL). The combined organic layers are dried with Na2SO4, filtered and concentrated. Purification of the crude material by chromatography gives the title compound (1.39 g, 5.18 mmol, 81%). 1H NMR (CDCl3): δ. 2.58 (s, 3H), 2.75 (s, 3H), 7.53 (t, J=7.9 Hz, 1H), 7.96 (d, J=7.9 Hz, 1H), 7.99 (d, J=7.5 Hz, 1H) ppm. ES-MS (m/z): calcd for C11H9BrOS (M+1)+: 270.2. found: 270.0.

Workup

  1. waitat rt for 10 min
  2. temperatureIt is cooled to 0° C.
  3. customquenched with sat. NH4C (10 mL)
  4. additiondiluted with H2O (20 mL)
  5. additiontreated with 0.1 M HCl (20 mL)
  6. extractionextracted with EtOAc (2×40 mL)
  7. dry with materialThe combined organic layers are dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the crude material by chromatography

Sources & evidence

ORD record
ord-84ea0813d27e40e4983dd2c80e0da747
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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