2-Bromobenzenethiol → HCID 66842178, compound

HRID 1158832Notes

Reaction equation

HRID 1158832 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]([O:13][C:14](=[O:35])[N:15]([C:17]1[CH:25]=[C:24]2[C:20]([CH:21]=[CH:22][N:23]2[CH2:26][C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=2)=[CH:19][CH:18]=1)[CH3:16])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])O.[Na+]>ClCCl.C(OCC)C>[C:9]([O:13][C:14](=[O:35])[N:15]([C:17]1[CH:25]=[C:24]2[C:20]([C:21]([S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Br:1])=[CH:22][N:23]2[CH2:26][C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=2)=[CH:19][CH:18]=1)[CH3:16])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 805982-BromobenzenethiolHCID 516892Sodium BicarbonateHCID 66841803HCID 66841803, compound

Product 1

HCID 66842178HCID 66842178, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

—Sulfuryl chloride (1.08 ml, 13.4 mmol) was added to a solution of 2-bromobenzenethiol (1.27 g, 6.69 mmol) in dichloromethane (45 ml). The reaction mixture was stirred at room temperature for 15 min. and concentrated under reduced pressure. The resulting material was dissolved in diethyl ether and added dropwise to a solution of [1-(3,5-difluoro-benzyl)-1H-indol-6-yl]-methyl-carbamic acid tert-butyl ester (Example 6, method 1, step i; 2.50 g, 6.71 mmol) in diethyl ether (45 ml). The reaction mixture was stirred for 3.5 h and then poured into a saturated aqueous solution of sodium hydrogencarbonate. The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (heptane/ethyl acetate 9:1→8:2) afforded [3-(2-bromo-phenylsulfanyl)-1-(3,5-difluoro-benzyl)-1H-indol-6-yl]-methyl-carbamic acid tert-butyl ester (3.02 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting material was dissolved in diethyl ether
  3. stirringThe reaction mixture was stirred for 3.5 h
  4. extractionThe product was extracted into ethyl acetate
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd7626e37cd24b5da0ddea0673e71d5c
Source dataset
uspto-grants-2010_10
Patent number
US07812036B2

Reaction notes

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