Pyridine → HCID 53983011, compound

HRID 1873197Notes

Reaction equation

HRID 1873197 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:14][C:15]1[CH:32]=[C:31]([C:33]2[C:42]3[C:43]4[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=4[S:45][C:41]=3[C:40]([Br:50])=[C:39]3[C:34]=2[CH:35]=[CH:36][CH:37]=[CH:38]3)[CH:30]=[C:29]([Br:51])[C:16]=1[O:17][C@H:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19]([NH2:21])=O.N1C=CC=CC=1.O1CCOCC1>CCOCC>[Br:14][C:15]1[CH:32]=[C:31]([C:33]2[C:42]3[C:43]4[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=4[S:45][C:41]=3[C:40]([Br:50])=[C:39]3[C:34]=2[CH:35]=[CH:36][CH:37]=[CH:38]3)[CH:30]=[C:29]([Br:51])[C:16]=1[O:17][C@H:18]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:19]#[N:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 21970376HCID 21970376, compound

Product 1

HCID 53983011HCID 53983011, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
105 °C

Procedure

Trifluoroacetic anhydride (0.375, 2.65 mmol) was added to a stirred, room temperature suspension of (R)-2- [2,6-dibromo-4-(6-bromo-benzo[b]naphtho [2,3-d ]thiophen-11-yl)-phenoxy]-3-phenyl-propionamide (1.68 g, 2.37 mmol), pyridine (0.393 mL, 4.74 mmol) and dioxane (5.4 mL). Dissolution occurred and the solution was heated in a 105° C. oil bath for 2 h. The reaction mixture was cooled to room temperature, diluted with ether, washed with 5% HCl and brine. Silica gel was added to the ether phase and the solvent was removed. The adsorbate was flash chromatographed (ether as eluent) to provide the title compound as a white solid (1.38 g, 84%): mp 160-165° C.: NMR (DMSO-d6): δ8.29 (d, J=8 Hz, 1 H), 8.07 (d, J=8 Hz, 1 H), 7.93 (d, J=2 Hz, 1 H), 7.91 (d, J=2 Hz, 1 H), 7.80 (ddd, 8, 7, 1 Hz, 1 H), 7.65-7.33 (m, 8 H), 7.23 (ddd, 8, 7, 1 Hz, 1 H), 6.65 (d, J=8 Hz, 1 H), 5.87 (t, J=7 Hz, 1 H), 3.58 (m, 2 H); MS (EI): [M+], 3 bromine isotope pattern, 689 (30%), 691 (95%) 693 (100%) 695 (40%); Anal. Calc. for C31H18Br3NOS: C, 53.74, H, 2.62, N, 2.02. Found: C, 53.60, H, 2.60, N, 1.83.

Workup

  1. dissolutionDissolution
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with 5% HCl and brine
  4. additionSilica gel was added to the ether phase
  5. customthe solvent was removed
  6. customchromatographed (ether as eluent)

Sources & evidence

ORD record
ord-2b8aa4c4a1bb487ab91aa56a79905e65
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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