Bromine → HCID 58032604, compound

HRID 2200932Notes

Reaction equation

HRID 2200932 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[N:16][N:17]=[C:13]3[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:11]([CH3:28])=[C:10]2[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:5][CH:4]=1)#[N:2].[Br:34]Br>C(Cl)(Cl)Cl>[Br:34][CH2:28][C:11]1[N:12]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:13]2[N:14]([N:15]=[N:16][N:17]=2)[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[C:10]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

4

Reactant 2

HCID 24408BromineHCID 46841075HCID 46841075, compound

Product 1

HCID 58032604HCID 58032604, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

Ethyl 7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate (30 mg, 66.1 μmol; Example 70) was dissolved in chloroform (1 ml), and a solution of bromine (3×11.6 mg, 3×72.6 μmol, 3.3 eq.) in chloroform was added a little at a time at 0° C. The mixture was then stirred for 12 h, during which time it slowly warmed to RT. The mixture was then diluted with chloroform and washed with 10% strength sodium thiosulfate solution. The organic phase was separated off, dried over sodium sulfate and, after filtration, concentrated on a rotary evaporator. The crude product was reacted further without further purification (35.3 mg, 87% pure according to LC-MS, 87% of theory).

Workup

  1. washwashed with 10% strength sodium thiosulfate solution
  2. customThe organic phase was separated off
  3. dry with materialdried over sodium sulfate
  4. filtrationafter filtration
  5. concentrationconcentrated on a rotary evaporator
  6. customThe crude product was reacted further without further purification (35.3 mg, 87% pure according to LC-MS, 87% of theory)

Sources & evidence

ORD record
ord-e5e5c73b47334ac88e4ed4abb87ae845
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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