N-bromobutanimide → HCID 67499595, compound

HRID 1484732Notes

Reaction equation

HRID 1484732 reaction equation
[CH3:1][N:2]([C:10]1[CH:11]=[N:12][N:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:14]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[Br:21]N1C(=O)CCC1=O>ClC(Cl)C>[Br:21][C:14]1[N:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:12]=[CH:11][C:10]=1[N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67499598HCID 67499598, compound

Product 1

HCID 67499595HCID 67499595, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To tert-butyl methyl(1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (0.200 g, 0.729 mmol) in dichloroethane (3.65 ml) was added 1-bromopyrrolidine-2,5-dione (0.260 g, 1.458 mmol) and the reaction was stirred overnight at 50° C. The reaction was concentrated, diluted with dichloromethane, and washed with water and saturated aqueous sodium thiosulfate. The organic phase was concentrated to give tert-butyl 5-bromo-1-(pyridin-3-yl)-1H-pyrazol-4-yl(methyl)carbamate (256 mg, 0.725 mmol, 99%) as a brown oil: IR (thin film) 1697 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.68 (d, J=4.1 Hz, 1H), 7.93 (ddd, J=8.2, 2.5, 1.5 Hz, 1H), 7.69 (s, 1H), 7.46 (dd, J=8.1, 4.8 Hz, 1H), 3.22 (s, 3H), 1.44 (s, 9H); ESIMS m/z 352 ([M−H]−).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with dichloromethane
  3. washwashed with water and saturated aqueous sodium thiosulfate
  4. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-a62bc59a35954dd19a04e929529fcbff
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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