Ethyl Bromide → HCID 90033749, compound

HRID 2274999Notes

Reaction equation

HRID 2274999 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9][C:6]2=[N:7][CH:8]=1.[OH-].[K+].Br[CH2:20][CH3:21]>CS(C)=O>[CH2:20]([N:9]1[C:6]2=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[CH:11]=[C:10]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:21]

Participants

5

Reactant 3

HCID 6332Ethyl Bromide2×HCID 14797Potassium HydroxideHCID 59754779HCID 59754779, compound

Product 1

HCID 90033749HCID 90033749, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of ethyl 5-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (150 mg, 0.68 mmol available, for example, from Shanghai Haoyuan Chemexpress Co., Ltd) in DMSO (4 ml) was added powdered potassium hydroxide (115 mg, 2.04 mmol) followed by bromoethane (0.071 ml, 0.95 mmol). The mixture was stirred at rt for 2 hr then further bromoethane (0.020 ml) was added and the mixture stirred for a further 18 hr. The reaction was quenched by the addition of water then partitioned between water and diethyl ether. The organic phase was washed with water then passed through a hydrophobic frit and finally concentrated under reduced pressure to give the product as an orange/brown oil. The crude material was purified with column chromatography (eluted with DCM and ethyl acetate from 0 to 10%) to give the title compound as clear oil (60 mg, 36%).

Workup

  1. stirringthe mixture stirred for a further 18 hr
  2. customThe reaction was quenched by the addition of water
  3. customthen partitioned between water and diethyl ether
  4. washThe organic phase was washed with water
  5. concentrationfinally concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f9f83919f134d359729f2bdd99b290d
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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