Bromine → HCID 66730892, compound

HRID 1028016Notes

Reaction equation

HRID 1028016 reaction equation
[F:1][C:2]([F:33])([F:32])[C@H:3]([NH:5][S:6]([C:9]1[CH:10]=[N:11][C:12]([C:15]2[N:16]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:17]3[C:22]([C:23]=2[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([CH3:26])[CH:18]=3)=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH3:4].[Br:34]Br>O>[F:33][C:2]([F:1])([F:32])[C@H:3]([NH:5][S:6]([C:9]1[CH:10]=[N:11][C:12]([C:15]2[N:16]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[C:17]3[C:22]([C:23]=2[C:24]#[N:25])=[CH:21][C:20]([Br:34])=[C:19]([CH3:26])[CH:18]=3)=[CH:13][CH:14]=1)(=[O:7])=[O:8])[CH3:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 66730864HCID 66730864, compound

Product 1

HCID 66730892HCID 66730892, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (R)-6-(3-cyano-1-cyclopentyl-6-methyl-1H-indol-2-yl)-pyridine-3-sulfonic acid (2,2,2-trifluoro-1-methyl-ethyl)-amide (0.48 g, 1.05 mmol) in acidic acid (3 mL) was added bromine (0.35 g, 2.1 mmol) dropwise. The solution was stirred at 90° C. for 30 min, cooled to room temperature and then diluted with water (20 mL). The precipitate was collected and washed thoroughly with water, then dried to give (R)-6-(5-bromo-3-cyano-1-cyclopentyl-6-methyl-1H-indol-2-yl)-pyridine-3-sulfonic acid (2,2,2-trifluoro-1-methyl-ethyl)-amide as a light yellow solid (0.54 g, 93%).

Workup

  1. temperaturecooled to room temperature
  2. customThe precipitate was collected
  3. washwashed thoroughly with water
  4. customdried

Sources & evidence

ORD record
ord-d19f4a453a8f4241865d3c603e589402
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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