Tetrabutylammonium Fluoride → HCID 58914725, compound

HRID 1297779Notes

Reaction equation

HRID 1297779 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+].[CH3:45][O:46][C:47]1[CH:48]=[C:49]([CH:52]=[CH:53][CH:54]=1)[CH2:50]Br.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:9]=[C:8]([CH3:32])[C:7]([OH:6])=[C:12]([CH3:13])[CH:11]=2)([CH2:50][C:49]2[CH:52]=[CH:53][CH:54]=[C:47]([O:46][CH3:45])[CH:48]=2)[C:15]1=[O:31]

Participants

6

Reactant 4

HCID 2724141Tetrabutylammonium FluorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 40672073-Methoxybenzyl bromideHCID 58914697HCID 58914697, compound

Product 1

HCID 58914725HCID 58914725, compoundYield 95.9%

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 (250 mg, 0.51 mmol), a 0.5M solution of potassium bis(trimethylsilyl)amide (1.04 mL, 0.52 mmol), and 3-methoxybenzyl bromide (0.073 mL, 0.31 mmol) in DMF (5 mL) followed by treatment with TBAF (0.56 mL, 0.56 mmol) gives a crude yellow solid. Purify by flash chromatography (gradient of 50% hexanes/CH2Cl2 to CH2Cl2) to give 148 mg (58%) of the title compound as a yellow powder. MS (ES): m/z=498 (M+1), 496 (M−1); 1H NMR(DMSO-d6); δ8.28 (s, 1H), 7.56 (m, 1H), 7.45 (dd, J=1.0 Hz, J=8.0 Hz, 1H), 7.24 (m, 1H), 7.14 (m, 2H), 7.00 (s, 2H), 6.85-6.76 (m, 3H), 6.64 (d, J=8.7 Hz, 2H), 6.50 (m, 1H), 5.68 (d, J=6.6 Hz, 1H), 4.79 (abq, J=17.1 Hz, 2H), 3.68 (s, 3H), 3.60 (d, J=12.7 Hz, 1H), 2.15 (s, 6H).

Workup

  1. customgives a crude yellow solid
  2. customPurify by flash chromatography (gradient of 50% hexanes/CH2Cl2 to CH2Cl2)

Sources & evidence

ORD record
ord-66f3dcb4e6c842ea8026de1cac823414
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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