Dichloromethane → HCID 22482337, compound

HRID 2181850Notes

Reaction equation

HRID 2181850 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH2:27][CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=3)[C:4]=2[CH:3]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.ClCCl.[OH-].[Na+]>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:27]([CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=2)[C:4]2[CH:3]=[C:2]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:15]=[CH:14][C:13]=2[N:12]1[S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:17])=[O:18])[CH3:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 66827Phenylboronic AcidHCID 224823412-Bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

Product 1

HCID 22482337HCID 22482337, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (Example 44, Step c, 0.25 g, 0.52 mmol) and phenylboronic acid (0.06 g, 0.52 mmol) in tetrahydrofuran (5 mL) was treated under nitrogen with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.01 g, 0.02 mmol) and a 5 N aqueous sodium hydroxide solution (0.2 mL, 1 mmol). The reaction mixture was heated at reflux for twelve hours, cooled to room temperature, and quenched with a saturated, aqueous, sodium chloride solution (10 mL) and diethyl ether (50 mL). The separated organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to a crude product. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4) to yield the title compound as a solid (0.13 g, 50%);

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for twelve hours
  3. customquenched with a saturated, aqueous, sodium chloride solution (10 mL) and diethyl ether (50 mL)
  4. dry with materialThe separated organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a crude product
  7. customThe crude product was purified by flash column chromatography on silica gel
  8. washeluting with a mixture of ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-0b5c1046c6094d2eb1890e079860633c
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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