Hydrogen Bromide → 2-Methyl-5,6-dihydro-4H-pyrrolo[3,4-d][1,3]thiazole

HRID 2353431Notes

Reaction equation

HRID 2353431 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH2:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:7][C:5]=2[N:6]=1.C1(O)C=CC=CC=1.Br.CCOCC>O>[CH3:1][C:2]1[S:3][C:4]2[CH2:9][NH:8][CH2:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 996PhenolHCID 3283Diethyl EtherHCID 15231190HCID 15231190, compound

Product 1

HCID 152311912-Methyl-5,6-dihydro-4H-pyrrolo[3,4-d][1,3]thiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To the product from Step B (100 mg) was added phenol (32 mg) followed by hydrogen bromide solution in water (48%, 2 mL). The mixture was refluxed for 90 min and cooled to ambient temperature Water (2 mL) and ether (5 mL) were added and the mixture stirred for 10 min and the ether layer removed. This wash was repeated and the aqueous layer was then treated with acetonitrile and filtered to give a pale brown solid. The solid was purified by preparative thin layer chromatography using an Analtech® 1500 micron plate (10% methanol/ethyl acetate, 1% ammonium hydroxide) to give the title compound as a dark solid. LC/MS 141.1 (M+1).

Workup

  1. temperatureThe mixture was refluxed for 90 min
  2. additionwere added
  3. customthe ether layer removed
  4. additionthe aqueous layer was then treated with acetonitrile
  5. filtrationfiltered
  6. customto give a pale brown solid
  7. customThe solid was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-62f8873b3add4af0a8800ba183f5c086
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

Loading…