Potassium Carbonate → HCID 57705593, compound

HRID 1662434Notes

Reaction equation

[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2OS(C(F)(F)F)(=O)=O)[C:10]([O:12][CH3:13])=[O:11])[CH2:3][CH2:2]1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)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>[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:14]=[CH:15][C:16]=2[C:27]2[CH:28]=[C:29]([O:32][CH3:33])[CH:30]=[CH:31][C:26]=2[F:25])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 66.46E (555 mg, 1.52 mmol) in DMF (10 mL) at 23° C. was added 2-fluoro-5-methoxyphenylboronic acid (512.3 mg, 3.0 mmol) (commercially available from Aldrich) and potassium carbonate (630.1 mg, 4.56 mmol) followed by tetrakis(triphenylphosphine)palladium(0) (176.8 mg, 0.15 mmol). The mixture was heated to 90° C. After 18 hours, LCMS showed the reaction was complete. The mixture was cooled to room temperature and diluted with water. After extracting three times with EtOAc, the mixture was concentrated in vacuo, and the residue was purified on silica gel (0-50% EtOAc in hexanes) to afford 66.46F (452.7 mg, 87% yield). MS ESI (pos.) m/e: 343.0 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
extractionAfter extracting three times with EtOAc
concentrationthe mixture was concentrated in vacuo
customthe residue was purified on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-51220ba5b6fc482eaf3f6f06d0efa8d8
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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