Sodium Carbonate → HCID 86722011, compound

HRID 1398056Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][C:11]([CH:22]2[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][C:24]([CH3:31])([CH3:30])[CH2:23]2)=[N:10]1.[CH2:32]([O:39][C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1.C(O)C>CCOC(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>[CH2:32]([O:39][C:40]1[CH:45]=[CH:44][C:43]([C:13]2[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:10]=[C:11]([CH:22]3[CH2:23][C:24]([CH3:31])([CH3:30])[O:25][C:26]([CH3:28])([CH3:29])[CH2:27]3)[CH:12]=2)=[CH:42][CH:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A flask was charged with trifluoro-methanesulfonic acid 2-(2-methoxy-phenyl)-5-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl ester (354 mg, 0.69 mmol) (Example 1, step E),4-(benzyloxy)phenylboronic acid (238.3 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.035 mmol), 2M Na2CO3 (2.8 mL) and 2:1 toluene/ethanol (10 mL) and the mixture was heated at 80° C. for 6 hrs. The resulting mixture was diluted with EtOAc and washed with sat. NaCl. EtOAc was removed under vacuum and the residue was purified by silica column chromatography to give 257.8 mg (74.5%) of the title compound.

Workup

washwashed with sat. NaCl
customEtOAc was removed under vacuum
customthe residue was purified by silica column chromatography

Sources & evidence

ORD record: ord-dc9fb2eef6244dbc95e6a9910e569e22
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901314B2

Reaction notes

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