Sodium Carbonate → HCID 178434670, compound

HRID 1959855Notes

Reaction equation

HRID 1959855 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-76814fd16fdd43bda0b0e8ca3faf83e8
Source dataset
uspto-grants-2013_04
Patent number
US08410272B2

Reaction notes

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