Bromine → HCID 58019866, compound

HRID 2200073Notes

Reaction equation

HRID 2200073 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.[Br:25]Br>ClCCl>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:25])[N:6]2[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 58019863HCID 58019863, compound

Product 1

HCID 58019866HCID 58019866, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of example 3 (700 mg) is dissolved in dichloromethane (400 mL) and bromine (7 mL) is added dropwise. The mixture is stirred overnight at room temperature and extracted with aqueous sodium thiosulfate (2 L of 0.1 M) solution and then with aqueous sodium bicarbonate (500 mL, saturated). The residue from the organic layer is chromatographed on silica gel using 3% methanol in dichloromethane) to yield 460 mg of bromo product. NMR, UV and MS are consistent with structure assignment.

Workup

  1. extractionextracted with aqueous sodium thiosulfate (2 L of 0.1 M) solution
  2. customThe residue from the organic layer is chromatographed on silica gel using 3% methanol in dichloromethane)
  3. customto yield 460 mg of bromo product

Sources & evidence

ORD record
ord-7bc3a11604e24a9e8e2da75ad89df163
Source dataset
uspto-grants-2016_06
Patent number
US09359360B2

Reaction notes

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