Cesium carbonate → HCID 87113365, compound

HRID 1672547Notes

Reaction equation

HRID 1672547 reaction equation
FC(F)(F)C(O[C:6]1[C:15]2[CH2:14][C@H:13]([O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=O.[C:36](=[NH:49])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Si:17]([O:16][C@H:13]1[CH2:14][C:15]2[C:6]([N:49]=[C:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:11][CH2:12]1)([C:30]([CH3:32])([CH3:31])[CH3:33])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 66696622HCID 66696622, compound

Product 1

HCID 87113365HCID 87113365, compoundYield 85.4%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Example 26D (291 mg, 0.544 mmol), benzophenone imine (0.18 mL, 1.1 mmol), cesium carbonate (390 mg, 1.20 mmol), tris(dibenzylideneacetone)dipalladium(0) (14 mg, 0.015 mmol), and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (22 mg, 0.035 mmol) in dimethoxyethane (2.2 mL) was heated at 150° C. for 25 minutes in a microwave reactor. The mixture was cooled to room temperature, and the solution was pipetted away from the residual solid and concentrated. Chromatography of the resulting residue on silica gel (1 to 5% ethyl acetate-hexane, eluant) afforded 263 mg (85% yield) of the title compound as a sticky yellow oil/foam. 1H NMR (300 MHz, DMSO-d6) δ 7.19-7.74 (m, 18H), 6.92 (m, 2H), 6.77 (m, 1H), 6.60 (m, 1H), 6.18 (m, 1H), 4.12 (m, 1H), 2.53-2.62 (m, 3H), 2.38 (m, 1H), 1.84 (m, 1H), 1.72 (m, 1H), 0.99 (s, 9H). MS (DCI+) m/z 566 (M+H)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-170bad82451243619c1332e283e76845
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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