Trimethylsilyl iodide → HCID 16654939, compound

HRID 1019604Notes

Reaction equation

HRID 1019604 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 uL). After heating for ½ hour at 70° C., another 200 uL 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 1M 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 1M 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-5743fad2c4744dac8c5529c68cb3ef33
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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