1-Naphthalenesulfonyl chloride → HCID 11509961, compound

HRID 1868410Notes

Reaction equation

HRID 1868410 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]([NH2:14])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:17]1([S:27](Cl)(=[O:29])=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1.CCOCC>[F:16][C:2]([F:1])([F:15])[CH:3]([NH:14][S:27]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:29])=[O:28])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1

Participants

5

Reactant 2

HCID 665601-Naphthalenesulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

Product 1

HCID 11509961HCID 11509961, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 100 mg (0.44 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 99 mg (0.44 mmol) of 1-naphthylsulfonyl chloride in 4 mL of pyridine was warmed at 70° C. After 3 hours, the mixture was cooled and concentrated to afford a thick oily residue. The residue was diluted with ether and washed twice with 10% aqueous acetic acid and brine, dried over sodium sulfate, decanted and concentrated in vacuo. The crude material was crystallized from ether-hexanes to afford 102 mg (55%) as off white needles, MS: m/z 419.3 (M+).

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated
  3. customto afford a thick oily residue
  4. washwashed twice with 10% aqueous acetic acid and brine
  5. dry with materialdried over sodium sulfate
  6. customdecanted
  7. concentrationconcentrated in vacuo
  8. customThe crude material was crystallized from ether-hexanes
  9. customto afford 102 mg (55%) as off white needles, MS

Sources & evidence

ORD record
ord-15550f1546a94254857e8b16360b8be8
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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