4-Fluorophenylboronic acid → HCID 131727380, compound

HRID 1788600Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:44]=[CH:43][C:9]2[N:10]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[C:18]([C:23]3[CH:28]=[C:27]([C:29]([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)=[O:30])[CH:26]=[CH:25][C:24]=3I)[CH:17]=[CH:16]4)=[N:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[F:45][C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1.C([O-])(O)=O.[Na+]>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>[CH2:1]([O:3][C:4]([C:6]1[CH:44]=[CH:43][C:9]2[N:10]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[C:18]([C:23]3[C:24]([C:49]5[CH:50]=[CH:51][C:46]([F:45])=[CH:47][CH:48]=5)=[CH:25][CH:26]=[C:27]([C:29]([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)=[O:30])[CH:28]=3)[CH:17]=[CH:16]4)=[N:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 200 mg (0.29 mmol) Compound 419d 62 mg (0.44 mmol) 4-fluorophenyl-boronic acid, 32 mg (0.029 mmol) Pd(PPh3)4 and 2 mL sat. NaHCO3 in 16 mL degassed MeOH was heated at 90° C. under Ar overnight. The mixture was evaporated to dryness, the residue was taken up in CH2Cl2 and purified on silica gel using CH2Cl21MeOH as eluent to yield 197 mg orange solid.

Workup

customdegassed MeOH
customThe mixture was evaporated to dryness
custompurified on silica gel using CH2Cl21MeOH as eluent

Sources & evidence

ORD record: ord-180008a4e1d843148585643ac69fb651
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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