Triethylsilane → HCID 58399557, compound

HRID 889497Notes

Reaction equation

HRID 889497 reaction equation
[CH2:1]([O:3][C:4]1[C:12]2[C:11](=O)[N:10]([C:14]3[C:19]([F:20])=[CH:18][C:17]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][C:15]=3[F:27])[CH:9]([OH:28])[C:8]=2[C:7]([O:29][CH2:30][CH3:31])=[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=12)[CH3:2].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:14]3[C:19]([F:20])=[CH:18][C:17]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][C:15]=3[F:27])[C:9](=[O:28])[C:8]=2[C:7]([O:29][CH2:30][CH3:31])=[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=12)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 58399574HCID 58399574, compound

Product 1

HCID 58399557HCID 58399557, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of ethyl {4-[4,9-bis(ethyloxy)-1-hydroxy-3-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3,5-difluorophenyl}acetate (0.240 g, 0.495 mmol) in TFA (3 ml) at 0° C. was added triethylsilane (0.118 ml, 0.742 mmol) drop wise. The bright red solution turned light yellow on addition. The mixture was evaporated then purified by MDAP. The fractions were evaporated to give a yellow solid (0.049 g, 0.10 mmol) LC/MS: Rt=3.62, [MH]+ 470.

Workup

  1. additionThe bright red solution turned light yellow on addition
  2. customThe mixture was evaporated
  3. customthen purified by MDAP
  4. customThe fractions were evaporated

Sources & evidence

ORD record
ord-4bd93e5d09a045239474a1aed7b1f33b
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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