Cyanogen Bromide → HCID 178422405, compound

HRID 1401253Notes

Reaction equation

HRID 1401253 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:5]=[C:4]([NH2:17])[C:3]=1[NH2:18].[N:19]#[C:20]Br>CO>[CH3:1][C:2]1[C:3]2[NH:18][C:20]([NH2:19])=[N:17][C:4]=2[CH:5]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 666077053-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

Product 1

HCID 178422405HCID 178422405, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine (See Example 1.G) (500 mg, 2.015 mmol) and cyanic bromide (0.484 mL, 2.418 mmol) were added to a round bottom flask at room temperature, suspended in methanol (10.0 mL) and allowed to stir for 1.5 h. Volatiles were removed under reduced pressure followed by the addition of saturated sodium bicarbonate. The precipitate was collected via filtration, washed with ethyl acetate and dried under reduced pressure to afford the title compound (557 mg, 2.039 mmol, quant. yield). Compound was carried forward without further purification or characterization. MS (ESI) m/z 273.8 [M+1]+.

Workup

  1. customVolatiles were removed under reduced pressure
  2. additionfollowed by the addition of saturated sodium bicarbonate
  3. filtrationThe precipitate was collected via filtration
  4. washwashed with ethyl acetate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0c84e443927140929bc42f0e79e66562
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

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