Trimethylsilyl iodide → HCID 54036048, compound

HRID 1873186Notes

Reaction equation

HRID 1873186 reaction equation
I[Si](C)(C)C.[Br:6][C:7]1[CH:31]=[C:30]([C:32]2[C:41]3[C:42]4[CH:48]=[CH:47][CH:46]=[CH:45][C:43]=4[S:44][C:40]=3[C:39](Br)=[C:38]3[C:33]=2[CH:34]=[CH:35][CH:36]=[CH:37]3)[CH:29]=[C:28]([Br:50])[C:8]=1[O:9][C@H:10]([CH2:15][CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27])[C:11]([O:13]C)=[O:12]>C(Cl)Cl>[CH:48]1[C:42]2[C:41]3[C:32]([C:30]4[CH:31]=[C:7]([Br:6])[C:8]([O:9][C@H:10]([CH2:15][CH2:16][N:17]5[C:18](=[O:27])[C:19]6[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=6)[C:25]5=[O:26])[C:11]([OH:13])=[O:12])=[C:28]([Br:50])[CH:29]=4)=[C:33]4[C:38](=[CH:39][C:40]=3[S:44][C:43]=2[CH:45]=[CH:46][CH:47]=1)[CH:37]=[CH:36][CH:35]=[CH:34]4

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 10819172HCID 10819172, compound

Product 1

HCID 54036048HCID 54036048, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodotrimethylsilane (0.203 mL, 1.43 mmol) was added to a rt, stirred solution of (R)-2-[2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid, methyl ester (0.770 g, 0.953 mmol) in methylene chloride (8 mL) under a dry nitrogen atmosphere. After 2 h, iodotrimethylsilane (3×0.203 mL, 4.29 mmol) was added to the resulted dark brown solution at rt three times every 12 h. The solution was quenched with water (0.4 mL), concentrated, chased with benzene (3×50 mL). The resulted residue was dissolved in ethyl acetate (60 mL) and silica gel (acid washed, 8 mL) was added. Solvent was removed and the adsorbate was flash chromatographed (eluent 7:3 pet. ether:ethyl acetate) to provide the title compound as a yellow solid (0.304 g, 45%): mp: 222-223° C.; NMR (CDCl3); δ8.37 (s, 1 H), 7.95(d, J=8 Hz, 1 H),7.89-7.85 (m, 2 H), 7.79 (dd, J=8,1 Hz, 1 H), 7.78-7.71 (m, 2 H), 7.64 (d, J=10 Hz, 1 H), 7.62 (d, J=10 Hz, 1 H), 7.59 (dd, J=8, 1 Hz, 1 H), 7.55 (ddd, J=8, 7, 1 Hz, 1 H), 7.46 (ddd, J=8, 7, 1 Hz, 1 H), 7.40 (ddd, J=8, 7, 1 Hz, 1 H), 7.19(ddd, J=8, 7, 1 Hz, 1 H), 6.88(d, J=8 Hz, 1 H), 5.27 (t, J=7 Hz, 1 H, 1 H, CH), 4.12 (m, 2 H), 2.65 (t, J=6 Hz, 2 H); MS (FAB-): [M-H]-, 2 bromine isotope pattern, 713, 714, 716; Anal. Calc. for C34H21Br2NO5S: C, 57.08, H, 2.96, N, 1.96. Found: C, 56.43, H, 2.74, N, 1.90.

Workup

  1. customThe solution was quenched with water (0.4 mL)
  2. concentrationconcentrated, chased with benzene (3×50 mL)
  3. dissolutionThe resulted residue was dissolved in ethyl acetate (60 mL)
  4. additionsilica gel (acid washed, 8 mL) was added
  5. customSolvent was removed
  6. customchromatographed (eluent 7:3 pet. ether:ethyl acetate)

Sources & evidence

ORD record
ord-453c90ccc73c42cf83685ffe7497dadd
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

Loading…