Cesium carbonate → HCID 69515353, compound
Reaction equation
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.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:54]1[N:59]=[CH:58][CH:57]=[CH:56][N:55]=1.[CH3:60][O:61][C:62]([C:64]1[C:65]([S:70][CH2:71][C:72]2[CH:77]=[CH:76][C:75]([Cl:78])=[CH:74][CH:73]=2)=[N:66][S:67][C:68]=1[NH2:69])=[O:63]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:60][O:61][C:62]([C:64]1[C:65]([S:70][CH2:71][C:72]2[CH:77]=[CH:76][C:75]([Cl:78])=[CH:74][CH:73]=2)=[N:66][S:67][C:68]=1[NH:69][C:54]1[N:59]=[CH:58][CH:57]=[CH:56][N:55]=1)=[O:63]Participants
Conditions
- Temperature
- 100 °C
Procedure
racemic 2,2′-Bis(diphenyl-phosphino)-1,1′-binaphthyl (87 mg, 0.14 mmol) is dissolved in toluene (4.5 mL) and then Tris(dibenzylideneacetone)-dipalladium (0) (44 mg, 0.05 mmol), Cesium carbonate (468 mg, 1.43 mmol), 2-bromopyrimidine (228 mg, 1.43 mmol), and compound 20 (300 mg, 0.96 mmol) are added. The reaction mixture is vigorously stirred at 100° C. for 4 hrs. The reaction is then filtered hot and washed with methylene chloride followed by hot dichloroethane (30 mL). The mother liquor is then concentrated in vacuo and triturated with MeOH to obtain a crude solid which is recrystalized from dichloroethane to provide 21 (265 mg, 71%). 1H NMR (d6 DMSO): δ 10.72 (1H, s), 8.79 (2H, d, J=5.0 Hz), 7.44 (2H, d, J=8.2 Hz), 7.34 (2H, d, J=8.2 Hz), 7.23 (1H, dd, J=5.0, 5.0 Hz), 4.35 (2H, s), 3.86 (3H, s).
Workup
- filtrationThe reaction is then filtered hot
- washwashed with methylene chloride
- concentrationThe mother liquor is then concentrated in vacuo
- customtriturated with MeOH
- customto obtain a crude solid which
- customis recrystalized from dichloroethane
Sources & evidence
- ORD record
- ord-fd3c57dd573d497ba57886afe38f0d2a
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07276602B2
Reaction notes
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