Potassium Phosphate, Tribasic → HCID 118324111, compound

HRID 1778294Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH:28](/B(O)O)=[CH:29]\[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]=[CH:4][CH:3]=[C:2]3/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[OH:13])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of (4-bromoquinolin-6-yl)bis(4-chlorophenyl)methanol (50 mg, 0.109 mmol), (E)-styrylboronic acid (25.8 mg, 0.17 mmol), Pd(OAc)2 (2.44 mg, 0.0109 mmol), SPhos (8.9 mg, 0.022 mmol) and K3PO4 (46 mg, 0.218 mmol) was warmed to 30° C. for 7 hr under argon and then stirred at room temperature overnight. The reaction was quenched with water. The solids were filtered. The aqueous layer was extracted with EtOAc twice. The organic layers and solids (which were dissolved in EtOAc) together were concentrated and the crude material was purified by silica column chromatography (35% EtOAc/hexanes) to yield (E)-bis(4-chlorophenyl)(4-styrylquinolin-6-yl)methanol. (M+H)+: 482, 484.

Workup

customThe reaction was quenched with water
filtrationThe solids were filtered
extractionThe aqueous layer was extracted with EtOAc twice
dissolutionThe organic layers and solids (which were dissolved in EtOAc)
concentrationtogether were concentrated
customthe crude material was purified by silica column chromatography (35% EtOAc/hexanes)

Sources & evidence

ORD record: ord-74e96600f88249e58903d9e5fb1c4aed
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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