Acetonitrile → HCID 53976005, compound

HRID 1275393Notes

Reaction equation

HRID 1275393 reaction equation
CS(O[CH2:6][CH2:7][C@H:8]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[CH:27]=1)[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:11]=[CH:10]1)(=O)=O.[C:33](#[N:35])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:19]([O:18][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[N:9]([C@@H:8]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[CH:27]=1)[CH2:7][CH2:6][C:33]#[N:35])[CH:10]=[CH:11]2)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 53748801HCID 53748801, compound

Product 1

HCID 53976005HCID 53976005, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 165872Tetrabutylammonium CyanideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3R)-3-(3-bromophenyl)-3-(7-benzyloxyindol-1-yl)propan-1-yl methanesulfonate (2.50 g, 4.86 mmol prepared as in Example 3, step (i)) and tetrabutylammonium cyanide (1.96 g, 7.30 mmol) in dry acetonitrile (40.0 ml) under nitrogen was heated under reflux for 24 h. The cooled solution was evaporated to yield an orange/brown oil which was taken up in ethyl acetate (200 ml), washed with water (3×100 ml), dried (Na2SO4) and the solvent removed in vacuo. Column chromatography (ethyl acetate--light petroleum (b.p. 40-60° C.), 1:4) gave the title compound as a pale yellow oil (1.60 g, 74%). [α]D19 -129 (c=0.005 gml-1, CHCl3); Vmax (thin film)/cm-1 3064, 3033, 2932, 2872, 2247 (CN), 1575; δH (270 MHz) 2.10 (2H, m 2×propyl 3-H); 2.38 (2H, m, 2×propyl 2-H); 5.09 (2H, q, CH2Ph, 2J=10.9 Hz); 6.39 (1H, dd, propyl 1-H, 3J1,2 =9.7, 3J1,2 =5.8 Hz); 6.55 (1H, d, 3-H, 3J3.2 =3.3 Hz); 6.70 (1H, d, 6-H, Jo =7.6 Hz); 6.83 (1H, d, 4-H, Jo =7.6 Hz); 7.00 (2H, m, 5-H, 5'-H); 7.05 (1H, d, 2-H, 3J2,3 =3.0 Hz); 7.15 (1H, s, 2'-H); 7.21 (1H, d, 6'-H, Jo =8.0 Hz); 7.30 (1H, d, 4'-H, Jo =8.6 Hz); 7.38 (5H, m, 5ArH).

Workup

  1. temperatureunder reflux for 24 h
  2. customThe cooled solution was evaporated
  3. customto yield an orange/brown oil which
  4. washwashed with water (3×100 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9102e84c1f154a27a64441f0d3d069fc
Source dataset
uspto-grants-2000_12
Patent number
US06160120

Reaction notes

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