4-Methoxybenzyl bromide → HCID 58914704, compound

HRID 1297780Notes

Reaction equation

HRID 1297780 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:54]=[CH:53][C:50]([CH2:51]Br)=[CH:49][CH:48]=1.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)([CH2:51][C:50]2[CH:53]=[CH:54][C:47]([O:46][CH3:45])=[CH:48][CH:49]=2)[C:15]1=[O:31]

Participants

6

Reactant 4

HCID 1650214-Methoxybenzyl bromideHCID 2724141Tetrabutylammonium FluorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 58914697HCID 58914697, compound

Product 1

HCID 58914704HCID 58914704, compoundYield 63.5%

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 (333 mg, 0.68 mmol), a 0.5M solution of potassium bis(trimethylsilyl)amide (1.38 mL, 0.69 mmol), and (4-methoxybenzyl bromide (0.094 mL, 0.69 mmol) in DMF (8 mL) followed by treatment with TBAF (0.75 mL, 0.75 mmol) gives a crude brown oil. Purify by flash chromatography (gradient of 50% hexanes/CH2Cl2 to CH2Cl2) to give material which still contains a second entity. Chromatograph again (step gradient of 5% EtOAc/hexanes, 20% EtOAc/hexanes, 33% EtOAc/hexanes) to give 215 mg (63%) of the title compound. MS (ES): m/z=498 (M+1), 496 (M−1); 1H NMR(DMSO-d6): δ8.26 (s, 1H), 7.55 (m, 1H), 7.54 (dd, J=0.9 Hz, J=8.0 Hz, 1H), 7.24 (m, 1H), 7.14 (m, 2H), 7.00 (m, 3H), 6.90 (m, 1H), 6.75 (dd, J=2.2 Hz, J=8.0 Hz, 1H), 6.52 (m, 2H), 6.40 (m, 1H), 5.76 (d, J=6.3 Hz, 1H), 4.79 (abq, J=17.2, 2H), 3.59 (q, J=12.9, 2H), 3.46 (s, 3H), 2.15 (s, 6H).

Workup

  1. customgives a crude brown oil
  2. customPurify by flash chromatography (gradient of 50% hexanes/CH2Cl2 to CH2Cl2)
  3. customto give material which

Sources & evidence

ORD record
ord-3c528dcb28c6447baa8a3628af72604e
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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