Bromine → HCID 68285498, compound

HRID 1518742Notes

Reaction equation

HRID 1518742 reaction equation
[Br:1]Br.C([NH:7][S:8]([C:11]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14]([C:21]2[C:25]([CH3:26])=[CH:24][S:23][C:22]=2[C:27]([O:29][CH3:30])=[O:28])=[CH:13][CH:12]=1)(=[O:10])=[O:9])(C)(C)C>ClCCl>[Br:1][C:24]1[S:23][C:22]([C:27]([O:29][CH3:30])=[O:28])=[C:21]([C:14]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=3[C:11]([S:8](=[O:10])(=[O:9])[NH2:7])=[CH:12][CH:13]=2)[C:25]=1[CH3:26]

Participants

4

Reactant 2

HCID 24408BromineHCID 68285474HCID 68285474, compound

Product 1

HCID 68285498HCID 68285498, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Bromine (0.045 g, 0.015 ml, 0.28 mmol) was added dropwise to a stirred suspension of methyl 3-(4-(N-(tert-butyl)sulfamoyl)-5,6,7,8-tetrahydronaphthalen-1-yl)-4-methylthiophene-2-carboxylate (59c, 0.10 g, 0.24 mmol) in 15 ml dichloromethane at a temperature of about 0° C. The reaction mixture was then stirred at about 25° C. for 2 hours. the progress of the reaction was monitored by TLC. The reaction mixture was then concentrated. 20 ml of dichloromethane was added to the residue so obtained. The mixture so formed was washed with water (2×10 ml), brine (1×10 ml) and the organic layer so obtained was dried over sodium sulfate. The dried organic layer was then concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 20% ethyl acetate in hexanes as an eluent to obtain the title compound (0.08 g, 67.4%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. addition20 ml of dichloromethane was added to the residue
  3. customso obtained
  4. customThe mixture so formed
  5. washwas washed with water (2×10 ml), brine (1×10 ml)
  6. customthe organic layer so obtained
  7. dry with materialwas dried over sodium sulfate
  8. concentrationThe dried organic layer was then concentrated under reduced pressure
  9. customto obtain a crude product, which
  10. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-98aef09b4f174576b6a5ea6e2355c48f
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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