Sodium Carbonate → HCID 178434670, compound

HRID 57295Notes

Reaction equation

HRID 57295 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]3[C:15]([CH3:16])=[N:14][NH:13][C:12]=3[NH2:17])=[N:8][C:7]=2[CH:18]=1.BrB(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[NH2:17][C:12]1[NH:13][N:14]=[C:15]([CH3:16])[C:11]=1[C:9]1[S:10][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:18][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 178488272HCID 178488272, compound

Product 1

HCID 178434670HCID 178434670, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

To a suspension of 4-(5-methoxy-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine (60 mg, 0.23 mmol) in CH2Cl2 (5 mL) at 4° C. was slowly added tribromoborane (2.3 mL of a 1M solution in dichloromethane, 2.3 mmol). The reaction temperature was maintained at 4° C. and the solution was stirred overnight. The mixture was then neutralized with sodium carbonate solution. The resulting solids were isolated by filtration and were purified by flash chromatography eluting with CHCl3:MeOH=9:1 to yield 10 mg (19%) of the title compound as a cream coloured solid. MS (m/z, ES+): 247.1 (M+1,100%).

Workup

  1. customThe resulting solids were isolated by filtration
  2. customwere purified by flash chromatography
  3. washeluting with CHCl3

Sources & evidence

ORD record
ord-ee25b137bb6b4cbbb78fc9470a309447
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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