Trimethylsilyl iodide → HCID 16654939, compound

HRID 1365608Notes

Reaction equation

HRID 1365608 reaction equation
C(OC([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([Br:21])=[C:14]([CH2:16][C:17]([F:20])([F:19])[F:18])[S:15][C:9]=2[CH2:8][CH2:7]1)=O)C.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[Br:21][C:13]1[C:10]2[CH2:11][CH2:12][NH:6][CH2:7][CH2:8][C:9]=2[S:15][C:14]=1[CH2:16][C:17]([F:19])([F:18])[F:20]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 66933877HCID 66933877, compound

Product 1

HCID 16654939HCID 16654939, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

The product of step (b) (0.18 mmol) was dissolved in CHCl3 (3 mL) and treated with TMSI (1 mmol, 200 μL). After heating for ½ hour at 70° C., another 200 μL of TMSI was added and heating was continued for ½ hour. The reaction was cooled and carefully quenched with 0.5 mL each of EtOH and water. The reaction was diluted with 1 M NaOH (3 mL) and the product was extracted into DCM (2×5 mL). The organic extracts were concentrated and the residue was purified by preparative HPLC-MS. 1H NMR (CD3OD) δ 3.75 (q, J=10.5 Hz, 2H), 3.43-3.34 (m, 4H), 3.26 (t, J=5.4 Hz, 2H), 3.16 (t, J=5.4 Hz, 2H), 3.16 (t, J=5.4 Hz, 2H); MS: ESI (positive): 316, 314 (M+H).

Workup

  1. temperatureheating
  2. temperatureThe reaction was cooled
  3. customcarefully quenched with 0.5 mL each of EtOH and water
  4. additionThe reaction was diluted with 1 M NaOH (3 mL)
  5. extractionthe product was extracted into DCM (2×5 mL)
  6. concentrationThe organic extracts were concentrated
  7. customthe residue was purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-82a39dd398634030a2ec90e6d302a348
Source dataset
uspto-grants-2011_02
Patent number
US07893051B2

Reaction notes

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