Sodium Bicarbonate → HCID 86667986, compound

HRID 1020855Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[C:6](I)[CH:5]=[CH:4][N:3]=1.[O:10]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.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>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:20]2[CH:21]=[CH:22][C:17]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:18][CH:19]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of intermediate compound D6 (0.5 g, 1.826 mmol) in 1,4-dioxane (11.25 ml) under a nitrogen atmosphere were added 4-phenoxyphenyl boronic acid [C.A.S. 51067-38-0] (0.469 g, 2.191 mmol), Pd(PPh3)4 (0.105 g, 0.0913 mmol) and NaHCO3 (3.75 ml, aqueous sat. solution). The reaction mixture was subjected to microwave heating at 150° C. for 5 min. After cooling, the mixture was filtered through a pad of diatomaceous earth and washed with EtOAc. The filtrate was evaporated in vacuo and the residue was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate compound D36 (0.498 g, 86%).

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through a pad of diatomaceous earth
washwashed with EtOAc
customThe filtrate was evaporated in vacuo
customthe residue was purified by column chromatography (silica gel; DCM as eluent)
customThe desired fractions were collected
customevaporated in vacuo
customto yield intermediate compound D36 (0.498 g, 86%)

Sources & evidence

ORD record: ord-528c73e985c44542934d9cc3d515247b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716480B2

Reaction notes

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