Methanol → HCID 90388153, compound

HRID 2205206Notes

Reaction equation

HRID 2205206 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:15][C:14]4[C:16]([O:20]C)=[CH:17][CH:18]=[CH:19][C:13]=4[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.B(Br)(Br)Br.CO>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:15][C:14]4[C:16]([OH:20])=[CH:17][CH:18]=[CH:19][C:13]=4[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 90388316HCID 90388316, compound

Product 1

HCID 90388153HCID 90388153, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloro-3-(7-methoxybenzo[b]thiophen-2-yl)imidazo[1,2-b]pyridazine (103 mg, 0.326 mmol, 1.0 equiv) in dichloromethane at −78° C. was added boron tribromide (2.27 mL, 1.0 M solution in dichloromethane, 7.0 equiv). The reaction mixture was stirred at the reduced temperature for 10 min then warmed to room temperature and stirred for 15 h. Methanol (2 mL) was added to quench the reaction and extracted with dichloromethane. Purification by column chromatography using 5% methanol in dichloromethane elution gave 70 mg of the yellow solid, 70%.

Workup

  1. stirringstirred for 15 h
  2. customto quench
  3. customthe reaction
  4. extractionextracted with dichloromethane
  5. customPurification by column chromatography
  6. wash5% methanol in dichloromethane elution

Sources & evidence

ORD record
ord-dd176d2ffa2a42e9ae6bc0ca5b74590f
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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