Trifluoroacetic acid → HCID 58238614, compound

HRID 1037649Notes

Reaction equation

HRID 1037649 reaction equation
C([SiH](CC)CC)C.[Br:8][C:9]1[N:14]=[C:13]([C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)[CH:12]=[CH:11][CH:10]=1.FC(F)(F)C(O)=O>ClCCl>[CH:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:8])[N:14]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 10830973HCID 10830973, compound

Product 1

HCID 58238614HCID 58238614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

At 0° C. triethylsilane (0.89 g, 7.7 mmol, 1.3 equiv) was added to compound 2 (2.0 g, 5.9 mmol, 1.0 equiv) in dichloromethane (50 mL). Trifluoroacetic acid (3.36 g, 29.5 mmol, 5.0 equiv) was added dropwise while maintaining the temperature<5° C. The reaction was allowed to warm to room temperature at which point the solution became a yellowish-green color. The reaction was stirred for 18 hr, LC/MS and TLC indicated the reaction was complete. The reaction was carefully quenched with saturated sodium bicarbonate (100 mL). The layers were separated, the organic layer was dried over sodium sulfate and absorbed onto silica gel (5 g) by concentration under reduced pressure. This material was purified on a silica gel column (25 g) by eluting with heptanes (250 mL) and ethyl acetate (2%) in heptanes (250 mL). The desired product was isolated pure in nearly quantitative yield (1.9 g).

Workup

  1. temperatureto warm to room temperature at which point the solution
  2. customThe reaction was carefully quenched with saturated sodium bicarbonate (100 mL)
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customabsorbed onto silica gel (5 g) by concentration under reduced pressure
  6. customThis material was purified on a silica gel column (25 g)
  7. washby eluting with heptanes (250 mL) and ethyl acetate (2%) in heptanes (250 mL)

Sources & evidence

ORD record
ord-3c906ffbc1b147639f91c05465bf2cca
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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