Chlorotriethylsilane → 2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole

HRID 1724031Notes

Reaction equation

HRID 1724031 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]([CH3:18])[CH2:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5].C1CCN2C(=NCCC2)CC1.[Si:32](Cl)([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34]>CN(C=O)C>[CH3:18][CH:13]1[CH2:12][C:11]2[C:15](=[CH:16][CH:17]=[C:9]([C:3]([O:8][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])([C:2]([F:1])([F:19])[F:20])[C:4]([F:7])([F:6])[F:5])[CH:10]=2)[NH:14]1

Participants

5

Reactant 3

HCID 13819Chlorotriethylsilane2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 233461261,1,1,3,3,3-hexafluoro-2-(2-methyl-2,3-dihydro-1H-indol-5-yl)-propan-2-ol

Product 1

HCID 210822122-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indoleYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.9 g (19.7 mmol) of 1,1,1,3,3,3-hexafluoro-2-(2-methyl-2,3-dihydro-1H-indol-5-yl)-propan-2-ol in DMF were added 2.94 mL (19.7 mmol) of DBU and after 30 min 3.3 mL (19.7 mmol) of TESCl. After 10 hrs, additional 0.44 mL (3.0 mmol) of DBU and 1.65 mL (9.85 mmol) of TESCl were added and stirring was continued for 2 hrs. The solvent and excess TESCl were evaporated i.v. and the residue was distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated to yield 8.1 g (99%) of 2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole, red liquid, MS: 414 (MH+).

Workup

  1. waitwas continued for 2 hrs
  2. customThe solvent and excess TESCl were evaporated i.v
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-5bec3546322640de91bb39df39446c69
Source dataset
uspto-grants-2009_02
Patent number
US07485652B2

Reaction notes

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