Nitrogen → 2-Bromo-5-(methoxymethyl)thiazole

HRID 82825Notes

Reaction equation

HRID 82825 reaction equation
N#N.[Br:3][C:4]1[S:5][C:6]([CH2:9][OH:10])=[CH:7][N:8]=1.[CH3:11]I>C(Cl)Cl>[Br:3][C:4]1[S:5][C:6]([CH2:9][O:10][CH3:11])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6328Methyl iodideHCID 7213124(2-Bromo-1,3-thiazol-5-yl)methanol

Product 1

HCID 587551802-Bromo-5-(methoxymethyl)thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (2-bromothiazol-5-yl)methanol (WO 2009/077990, p. 92) (1.19 g, 6.11 mmol) in CH2Cl2 (4.0 mL) was treated with MeI (0.46 mL, 7.33 mmol) followed by Ag2O (2.12 g, 9.16 mmol) and the resulting mixture (protected form light) was stirred overnight at 40° C. The reaction mixture was filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as a colorless oil: TLC: rf (7:3 hept-EA)=0.33. LC-MS-conditions 07: tR=0.66 min, [M+H]+=209.93.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (7:3 hept-EA)

Sources & evidence

ORD record
ord-018bec469cc84e9e864548c06d612296
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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