Dimethylformamide → Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-methyl-amine

HRID 1633637Notes

Reaction equation

HRID 1633637 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[C:18][CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH2:27]([CH2:30][NH2:31])[CH:28]=C.[CH3:32]N(C=O)C>>[CH2:30]([N:31]([CH2:21][CH2:20][CH2:19][C:18]#[C:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]=[CH:10]2)[CH3:32])[CH:27]=[CH2:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 86585584Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester

Product 1

HCID 18679475Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-methyl-amineYield 55%

Procedure

100 mg (0.26 mmol) Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester and 0.5 ml (5.2 mmol) N-allylmethylamine were stirred in 1 ml DMF at 60° C. for 1.5 h. The solution was concentrated, and the residue was dissolved in water and CH2Cl2. 2M NaOH was added and the inorganic phase was extracted with CH2Cl2. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 19:1 yielded 50 mg (55%) Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-methyl-amine as light yellow oil, MS: 347 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in water
  3. addition2M NaOH was added
  4. extractionthe inorganic phase was extracted with CH2Cl2
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-be46dcfaaabf4e31b326a40d363f1502
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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