Potassium Carbonate → HCID 53920431, compound

HRID 1067130Notes

Reaction equation

HRID 1067130 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][CH:16]=[C:15]2[C:20]2[O:21][C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH:8]=1)(=O)=O.B([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C:48]1[N:49]=[N:50][N:51]([C:53]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[N:52]=1)(O)O.C([O-])([O-])=O.[K+].[K+]>ClCCl.CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]1([C:23]2[N:24]=[C:20]([C:15]3[C@H:14]([CH2:13][C:9]4[CH:8]=[CH:7][CH:12]=[C:11]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=5[C:48]5[N:49]=[N:50][N:51]([C:53]([C:66]6[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=6)([C:60]6[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=6)[C:54]6[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=6)[N:52]=5)[CH:10]=4)[CH2:19][CH2:18][CH2:17][CH:16]=3)[O:21][C:22]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 9954488{2-[2-(Triphenylmethyl)-2H-tetrazol-5-yl]phenyl}boronic acidHCID 22961940HCID 22961940, compound

Product 1

HCID 53920431HCID 53920431, compoundYield 49.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenyl trifluoromethanesulfonate (1.17 g) in dichloromethane (100 ml) were added 5-(2-boronophenyl)-2-(triphenylmethyl)-2H-tetrazole (1.16 g), tetrakis(triphenylphosphine)palladium (600 mg), and K2CO3 (630 mg) in a mixture of DMF and water. After being stirred for 8 hours at 100° C., the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give (S)-2-(4,5-diphenyloxazol-2-yl)-1-{3-{2-[2-(triphenyl-methyl)tetrazol-5-yl]phenyl}benzyl}-2-cyclohexene (0.83 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f0a157ba91d94a2ea97f054aed2e3817
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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