Bromotrimethylsilane → HCID 21836681, compound

HRID 1379844Notes

Reaction equation

HRID 1379844 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[CH:5][CH:4]=1.C[Si]([Br:25])(C)C>C(Cl)Cl>[Br:25][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 21836659HCID 21836659, compound

Product 1

HCID 21836681HCID 21836681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the intermediate obtained in Step B in 4 mL of methylene chloride was treated with 0.16 mL (1.21 mmol) of trimethylsilylbromide. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with methylene chloride then washed with aqueous saturated sodium chloride (2×). The organic layer was dried over magnesium sulfate, filtered and evaporated under vacuum to yield 133 mg of crude product. 1H NMR (400 Hz, CDCl3): δ 2.78 (s, 6H), 4.5 (s, 2H), 6.4 (br s, 1H), 7.08 (t, 1H), 7.16 (dd, 1H), 7.34 (m, 4H), 7.49 (d, 1H), 8.10 (d, 1H).

Workup

  1. washthen washed with aqueous saturated sodium chloride (2×)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-936305ac8d544159bba2a7abe602b88c
Source dataset
uspto-grants-1997_09
Patent number
US05672596

Reaction notes

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