Trichloroacetonitrile → HCID 57546252, compound

HRID 913892Notes

Reaction equation

HRID 913892 reaction equation
C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[F:23][C:24]([F:46])([F:45])[C:25]1[CH:26]=[C:27]2[C:31](=[C:32]([CH:34]([OH:36])[CH3:35])[CH:33]=1)[N:30]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:29]=[CH:28]2.[Cl:47][C:48]([Cl:52])([Cl:51])[C:49]#[N:50]>C(OCC)C>[Cl:47][C:48]([Cl:52])([Cl:51])[C:49](=[NH:50])[O:36][CH:34]([C:32]1[CH:33]=[C:25]([C:24]([F:23])([F:45])[F:46])[CH:26]=[C:27]2[C:31]=1[N:30]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:44])[CH3:43])[CH:29]=[CH:28]2)[CH3:35]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 57546237HCID 57546237, compound

Product 1

HCID 57546252HCID 57546252, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diazabicycloundecene (33.0 mg, 0.217 mmol) was added to a solution of (±)-1-(5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-7-yl)ethanol (390 mg, 1.09 mmol) in diethyl ether (10 ml) and stirred for 10 min. Trichloroacetonitrile (235 mg, 1.627 mmol) was then added and the reaction stirred 16 h at ambient temperature. The solvent was evaporated and the residue purified by chromatography on silica gel with a gradient of ethyl acetate/hexanes from 5% to 40% to give 290 mg (53%) as a brown oil. 1H-NMR (CDCl3, 400 MHz) δ 8.23 (s, 1H), 7.82 (s, 1H), 7.69 (s, 1H), 7.17 (d, J=33 Hz, 1H), 6.76 (q, J=6.5 Hz, 1H), 6.57 (d, J=3.2 Hz, 1H), 6.19 (d, J=11.5 Hz, 1H), 5.30 (d, J=11.5 Hz, 1H), 3.48 (dd, J=9.0, 8.0 Hz, 2H), 1.75 (d, J=6.4 Hz, 3H), 0.92 (m, 2H), −0.07 (s, 9H); LC/MS (HPLC method 4): tR=4.31 min, 342.16(M-OC2NHCl3)+.

Workup

  1. stirringthe reaction stirred 16 h at ambient temperature
  2. customThe solvent was evaporated
  3. customthe residue purified by chromatography on silica gel with a gradient of ethyl acetate/hexanes from 5% to 40%
  4. customto give 290 mg (53%) as a brown oil

Sources & evidence

ORD record
ord-16c9ef8e18c14bda849e6923ef83f8eb
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

Loading…