Boron trifluoride → HCID 86693332, compound

HRID 575300Notes

Reaction equation

HRID 575300 reaction equation
O[C:2]1([CH3:22])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:5]=2[N:4]2[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:3]12.C([SiH](CC)CC)C.B(F)(F)F>ClCCl>[I:13][C:11]1[CH:10]=[CH:9][C:6]2[O:7][CH2:8][CH:2]([CH3:22])[C:3]3[N:4]([N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=3)[C:5]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 86693330HCID 86693330, compound

Product 1

HCID 86693332HCID 86693332, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 4-hydroxy-9-iodo-4-methyl-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate (2.3 g, 5.55 mmol, 1.00 equiv) in dichloromethane (50 mL) was added triethylsilane (9.7 g, 83.42 mmol, 15.00 equiv) and boron trifluoride diethyletherate (7.8 g, 10.00 equiv) at room temperature. After 1 h at room temperature the resulting mixture was diluted with 30 mL of dichloromethane, washed with saturated sodium bicarbonate solution, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:9) to give 370 mg (17%) of the titled compound as a light yellow solid; LC-MS (ES, m/z) 399 [M+H]+.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:9)

Sources & evidence

ORD record
ord-ca40b7dbef364547b5f942670b664c26
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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