Sodium Carbonate → HCID 58730613, compound

HRID 2233316Notes

Reaction equation

HRID 2233316 reaction equation
[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH:5]1[C:14]2[C:9](=[C:10]([F:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[N:6]1[C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[O:33][CH3:34].[F:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH:5]1[C:14]2[C:9](=[C:10]([F:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)=[CH:18][CH:17]=2)[N:6]1[C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[O:33][CH3:34]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 58730617HCID 58730617, compound

Product 1

HCID 58730613HCID 58730613, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Starting from 500 mg (0.91 mmol) of the bromide from Example 11A, reaction in analogy to general method [D] with 152.27 mg (1.09 mmol) of 4-fluorophenylboronic acid, 31.83 mg (0.05 mmol) of bis(triphenylphosphine)palladium(II) chloride and 115.34 mg (1.09 mmol) of sodium carbonate in 10 ml of 1,2-dimethoxyethane and 0.5 ml of water results in 370.7 mg (72% of theory) of the target compound.

Workup

  1. customresults in 370.7 mg (72% of theory) of the target compound

Sources & evidence

ORD record
ord-5e6c50dd55924705b1fc45e273e9c644
Source dataset
uspto-grants-2010_05
Patent number
US07709491B2

Reaction notes

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