Diisopropylethylamine → 6-Bromo-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole

HRID 1475326Notes

Reaction equation

HRID 1475326 reaction equation
[CH:1]([Si:4](OS(C(F)(F)F)(=O)=O)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[Br:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33]([CH3:39])([CH3:38])[CH2:34][NH:35]2)=[CH:31][C:30]=1[F:40]>C(Cl)Cl>[Br:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33]([CH3:38])([CH3:39])[CH2:34][N:35]2[Si:4]([CH:1]([CH3:2])[CH3:3])([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:9])[CH3:10])=[CH:31][C:30]=1[F:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 867239476-bromo-5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole

Product 1

HCID 867239466-Bromo-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indoleYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triisopropylsilyltrifluoromethanesulfonate (3.5 mL, 13.0 mmol) and DIPEA (3.2 mL, 19.5 mmol) were added to a solution of 6-bromo-5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole (1.5 g, 6.5 mmol) in DCM (50 mL). The reaction mixture was stirred at room temperature overnight then quenched with saturated aqueous NaHCO3 and extracted with DCM (×3). The organic phase was dried (MgSO4), filtered and concentrated. The crude material was purified by SiO2 chromatography (10% EtOAc in petrol) to give the title compound (1.8 g) as a white solid. 1H NMR (DMSO-d6): 7.07 (1H, d), 6.65 (1H, d), 3.44 (2H, s), 1.64-1.33 (3H, m), 1.33-1.17 (6H, m), 1.10 (18H, d).

Workup

  1. customthen quenched with saturated aqueous NaHCO3
  2. extractionextracted with DCM (×3)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by SiO2 chromatography (10% EtOAc in petrol)

Sources & evidence

ORD record
ord-963e24db7e9644a190154face561b808
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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