Boron tribromide → HCID 59823332, compound

HRID 1396820Notes

Reaction equation

HRID 1396820 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([NH:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21]([CH3:26])=[CH:20]4)[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)C.B(Br)(Br)Br>C(Cl)Cl>[CH3:26][C:21]1[NH:22][C:23]2[C:19]([CH:20]=1)=[CH:18][C:17]([NH:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C:5]3[CH:4]=[C:3]([OH:1])[CH:8]=[CH:7][CH:6]=3)[N:15]=1)=[CH:25][CH:24]=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 25104017HCID 25104017, compound

Product 1

HCID 59823332HCID 59823332, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N2-(3-methoxylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine (0.1mmol) in 5 ml CH2Cl2 was placed in an ice bath. To this was added BBr3(0.5 mmol). The reaction mixture was stirred overnight at room temperature, then poured into ice water, and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous Na2SO4, and concentrated. The residue was purified by column chromatography to provide the desired product in a yield of 83%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-95ca917e75b447638d55cbc00b1dbe8d
Source dataset
uspto-grants-2014_12
Patent number
US08901143B2

Reaction notes

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