Trimethylsilyl iodide → HCID 10629121, compound

HRID 1873187Notes

Reaction equation

HRID 1873187 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:49])=[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>[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:49])=[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:18](=[O:27])[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]1=[O:26])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 10819172HCID 10819172, compound

Product 1

HCID 10629121HCID 10629121, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodotrimethylsilane (2.8 mL, 1 N in methylene chloride) was added dropwise to a -10° C., 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 (14 mL) under a try N2 atmosphere. The solution was allowed to warm to ambient temperature and was stirred overnight. The reaction mixture was quenched, further diluted with water (100 mL), and partitioned between water and methylene chloride (2×75 mL). Methylene chloride extracts were concentrated and triturated with pet. ether. It was then recrystallized from acetic acid to provide the title compound as a grey solid (0.228 g, 52%): mp 215-217° C.: NMR (CDCl3); δ8.35 (d, J=8 Hz, 1 H), 7.89-7.86 (m, 2 H), 7.82 (dd, J=8, 1 Hz, 1 H), 7.76-7.71 (m, 2 H), 7.67(ddd, J=8, 7, 1 Hz, 1 H), 7.63-7.59 (m, 3 H), 7.58 (ddd, J=8, 7, 1 Hz, 1 H), 7.42 (ddd, J=8, 7, 1 Hz, 1 H), 7.20 (ddd, J=8, 7, 1 Hz, 1 H), 6.81(d, J=8 Hz, 1 H), 5.27 (t, J=7 Hz, 1 H, 1 H), 4.12 (m, 2 H), 2.65 (t, J =7 Hz, 2); MS (EI): [M+], 3 bromine isotope pattern, 791 (75%), 793 (98%), 795 (100%), 797 (38%); Anal. Calc. for C34H2OBr3NO5S: C, 51.41, H, 2.54, N, 1.76. Found: C, 51.65, H, 2.37, N, 1.70.

Workup

  1. customThe reaction mixture was quenched
  2. additionfurther diluted with water (100 mL)
  3. custompartitioned between water and methylene chloride (2×75 mL)
  4. concentrationMethylene chloride extracts were concentrated
  5. customtriturated with pet. ether
  6. customIt was then recrystallized from acetic acid

Sources & evidence

ORD record
ord-241e840900cd4d0cb1518879d5f732fb
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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