Hydrochloric Acid → HCID 10210746, compound

HRID 2307700Notes

Reaction equation

HRID 2307700 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[CH2:5][N:6]([C@@H:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH2:25]1)[C:7]([C:9]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:12]([C:18]([OH:20])=[O:19])=[CH:11][C:10]=1[C:21]([OH:23])=[O:22])=[O:8].[F:37][C:38]1[CH:39]=[CH:40][C:41]([O:47][CH3:48])=[C:42](B(O)O)[CH:43]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1COCC1.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>[F:37][C:38]1[CH:43]=[CH:42][C:41]([O:47][CH3:48])=[C:40]([C:2]2[CH:36]=[CH:35][CH:34]=[C:4]([CH2:5][N:6]([C@@H:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][CH2:25]3)[C:7]([C:9]3[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:12]([C:18]([OH:20])=[O:19])=[CH:11][C:10]=3[C:21]([OH:23])=[O:22])=[O:8])[CH:3]=2)[CH:39]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 10144017HCID 10144017, compound

Product 1

HCID 10210746HCID 10210746, compoundYield 27.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 15B (165 mg, 0.3 mmol), 5-fluoro-2-methoxyphenylboronic acid (68 mg, 0.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol) in THF (10 ml) were treated with 3M aqueous sodium carbonate (0.4 mL) and heated at reflux for 16 hours. After cooling to room temperature, the reaction mixture was diluted with water, acidified with 1N hydrochloric acid and extracted with diethyl ether. The organic layers were combined, dried with magnesium sulfate, filtered and the filtrate concentrated. The residue was purified by a Prep Nova Pak (HRC18) column using 0.1% trifluoroacetic acid:acetonitrile (10:90 to 95:5) as eluant to provide the title compound (50 mg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. extractionextracted with diethyl ether
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customThe residue was purified by a Prep Nova Pak (HRC18) column

Sources & evidence

ORD record
ord-68194434446a4b1e865db3984450f08f
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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