Potassium Carbonate → HCID 67091167, compound

HRID 2075686Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([O:18][CH2:19][C:20]3[CH:29]=[C:28]4[C:23]([C:24](Cl)=[CH:25][C:26]5[N:27]4[CH:30]=[N:31][N:32]=5)=[CH:22][CH:21]=3)[CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[N:34]1[CH:39]=[CH:38][CH:37]=[C:36](B(O)O)[CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.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>[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:12]=[C:13]([O:18][CH2:19][C:20]3[CH:29]=[C:28]4[C:23]([C:24]([C:36]5[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=5)=[CH:25][C:26]5[N:27]4[CH:30]=[N:31][N:32]=5)=[CH:22][CH:21]=3)[CH:14]=[C:15]([F:17])[CH:16]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To 5d (50 mg, 0.11 mmol) in DME:H2O (2:1, 2 mL) was added 3-pyridineboronic acid (20 mg, 0.16 mmol) and potassium carbonate (37 mg, 0.27 mmol). The mixture was degassed with N2 for 5 minutes, and then Pd(PPh3)4 (12 mg, 0.01 mmol) was added, and the mixture was degassed with N2 for an additional 5 minutes. The reaction was then heated to 80° C. overnight. After cooling to room temperature, the reaction was concentrated and purified by silica gel chromatography (10% MeOH in EtOAc) to give the desired product, 5e.

Workup

customThe mixture was degassed with N2 for 5 minutes
customthe mixture was degassed with N2 for an additional 5 minutes
temperatureAfter cooling to room temperature
concentrationthe reaction was concentrated
custompurified by silica gel chromatography (10% MeOH in EtOAc)

Sources & evidence

ORD record: ord-13ca0046b97e486aa4ca753655b81724
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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