Bromine → ethyl 3-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

HRID 573596Notes

Reaction equation

HRID 573596 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([CH3:23])[N:15]=[C:14]3[S:24][C:25]([C:27]4[CH:28]=[N:29][NH:30][CH:31]=4)=[CH:26][C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Br:32]Br>C(Cl)(Cl)Cl>[Br:32][C:26]1[C:13]2[C:14](=[N:15][C:16]([CH3:23])=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]=2[NH:11][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)(=[O:9])=[O:10])[S:24][C:25]=1[C:27]1[CH:28]=[N:29][NH:30][CH:31]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 68380155Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 68380308ethyl 3-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylateYield 90.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate (Description 73) (870 mg, 1.824 mmol) in CHCl3 (30 mL) at 60° C. was added bromine (0.10 mL, 2.01 mmol), prediluted in CHCl3 (5.25 mL), dropwise. The resulting mixture was stirred at 60° C. for ca. 4 h and was then cooled to RT. The resulting precipitate was filtered and the solid rinsed with DCM and dried, to give the title compound (920 mg). LCMS (A) m/z: 556/558 [M+1]+, Rt 1.25 min (acidic).

Workup

  1. temperaturewas then cooled to RT
  2. filtrationThe resulting precipitate was filtered
  3. washthe solid rinsed with DCM
  4. customdried

Sources & evidence

ORD record
ord-2a0f07f52b114f6295e6768a89c66c61
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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