Hydrochloric Acid → HCID 86585595, compound

HRID 1633710Notes

Reaction equation

HRID 1633710 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:18]#[C:19][CH2:20][CH2:21][CH2:22][OH:23].CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33].Cl>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[CH:4][C:3]=1[C:18]#[C:19][CH2:20][CH2:21][CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18679557HCID 18679557, compound

Product 1

HCID 86585595HCID 86585595, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 87 mg (0.28 mmol) 5-[6-Fluoro-1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol in 3 ml CH2Cl2 was treated with 0.14 ml (1 mmol) NEt3 and 80 μl (0.33 mmol) MsCl, stirred at room temperature for one hour, poured into icy 0.5 M aqueous HCl and extracted three times with Et2O. Drying of the combined organic layers with Na2SO4 and evaporation of the solvent gave (93 mg) Methanesulfonic acid 5-[6-fluoro-1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester as a light brown oil. 31 mg of this oil were dissolved in DMF, treated with 0.2 ml Allylmethylamine and the mixture stirred at 80° C. during 2 hours. Pouring the mixture into 0.5 M NaOH, extraction with CH2Cl2, drying of the organic layers with MgSO4, and flash chromatography with CH2Cl2/MeOH 19:1 gave 24 mg (89%) Allyl-{5-[6-fluoro-1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-methyl-amine as a light yellow oil, MS: 365 (MH+).

Workup

  1. extractionextracted three times with Et2O
  2. dry with materialDrying of the combined organic layers with Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-6a911d65aaeb43d68c48461bb9e86be4
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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