(3-Bromopropoxy)(tert-butyl)dimethylsilane → HCID 58914709, compound

HRID 1297778Notes

Reaction equation

HRID 1297778 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:15]2=[O:31])=[CH:9][C:8]=1[CH3:32])(C)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:46][CH2:47][CH2:48][O:49][Si](C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([C:10]2[CH:11]=[C:12]([CH3:13])[C:7]([OH:6])=[C:8]([CH3:32])[CH:9]=2)([CH2:46][CH2:47][CH2:48][OH:49])[C:15]1=[O:31]

Participants

6

Reactant 4

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 58914697HCID 58914697, compound

Product 1

HCID 58914709HCID 58914709, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a method similar to Example 37, with 3-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1-(2-chloro-benzyl)-1,3-dihydro-indol-2-one (150 mg, 0.31 mmol), a 0.5M solution of potassium bis(trimethylsilyl)amide (0.622 mL, 0.31 mmol), and (3-bromopropoxy)-tert-butyldimethylsilane (0.072 mL, 0.31 mmol) in DMF (3 mL) followed by treatment with TBAF (0.70 mL, 0.70 mmol) gives a crude brown gum. Purify by flash chromatography (gradient of 25% EtOAc/hexanes to 50% EtOAc/hexanes) to give 68 mg (51%) of the title compound as a pink solid. MS (ES): m/z=436 (M+1), 434 (M−1); 1H NMR(DMSO-d6): δ8.23 (s, 1H), 7.54 (dd, J=1.4 Hz, J=7.7 Hz, 1H), 7.37-7.22 (m, 4H), 7.12-7.04 (m, 2H), 6.90 (d, J=7.7 Hz, 1H), 6.83 (s, 2H), 5.05 (abq, J=16.7, 2H), 3.33 (m, under H2O), 2.27-2.18 (m, 2H), 2.11 (s, 6H), 1.23-0.99 (m, 2H).

Workup

  1. customgives a crude brown gum
  2. customPurify by flash chromatography (gradient of 25% EtOAc/hexanes to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dcaa8c96f49143da9e5fe7e639c63075
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

Loading…