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

HRID 573589Notes

Reaction equation

HRID 573589 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]3[CH:12]=[N:13][NH:14][CH:15]=3)=[CH:10][C:5]2=[C:4]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].[Br:31]Br>C(Cl)(Cl)Cl>[Br:31][C:10]1[C:5]2[C:6](=[N:7][C:2]([CH3:1])=[C:3]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:4]=2[NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[S:8][C:9]=1[C:11]1[CH:15]=[N:14][NH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 68380512Ethyl 6-methyl-4-[(phenylsulfonyl)amino]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 68324120ethyl 3-bromo-6-methyl-4-[(phenylsulfonyl)amino]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylateYield 89.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 6-methyl-4-[(phenylsulfonyl)amino]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate (Description 68) (5.8 g, 13.11 mmol) in CHCl3 (160 mL) at 60° C. was added bromine (0.81 mL, 15.73 mmol), pre-diluted in CHCl3 (36 mL), dropwise. The resulting mixture was stirred at 60° C. for ca. 1 h and then cooled to RT. The reaction mixture was then concentrated and the residue triturated with water (50 mL 3) and dried, to give the title compound (6.1 g). LCMS (A) m/z: 521/523 [M+1]+, Rt 1.11 min (acidic).

Workup

  1. temperaturecooled to RT
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue triturated with water (50 mL 3)
  4. customdried

Sources & evidence

ORD record
ord-17d3afbdf67f4d55a7c08e607a8a2c4e
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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