Boron tribromide → HCID 58362651, compound

HRID 2361460Notes

Reaction equation

HRID 2361460 reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([C:10]#[C:11][C:12]3[CH:19]=[CH:18][C:15]([NH:16][CH3:17])=[C:14]([N+:20]([O-:22])=[O:21])[CH:13]=3)[S:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:17][NH:16][C:15]1[CH:18]=[CH:19][C:12]([C:11]#[C:10][C:8]2[S:9][C:5]3[CH:4]=[C:3]([OH:2])[CH:24]=[CH:23][C:6]=3[N:7]=2)=[CH:13][C:14]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58362463HCID 58362463, compound

Product 1

HCID 58362651HCID 58362651, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask equipped with a magnetic stir bar containing DCM (5 vol) is placed 4-((6-methoxybenzo[d]thiazol-2-yl)ethynyl)-N-methyl-2-nitroaniline (1 equiv). The reaction mixture is cooled to 0° C., BBr3 (5 equiv of 1M in DCM) is added dropwise and the reaction is stirred at RT for 8 hours. The reaction is neutralized with sat. NaHCO3, extracted into DCM (2×5 vol). The combined organic extracts are washed with water (5 vol), brine (5 vol), dried over MgSO4 and concentrated in vacuo. The residue is purified over silica gel using EtOAc:Hexanes (1:3) as an eluent to afford the desired product.

Workup

  1. customTo a round bottomed flask equipped with a magnetic stir bar
  2. extractionextracted into DCM (2×5 vol)
  3. washThe combined organic extracts are washed with water (5 vol), brine (5 vol)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified over silica gel

Sources & evidence

ORD record
ord-8df7177ae4484d8c93f6ac16b844d695
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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