Dichloromethane → HCID 22482332, compound

HRID 2181860Notes

Reaction equation

HRID 2181860 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.[S:30]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31]1.ClCCl.[OH-].[Na+]>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:32]3[CH:33]=[CH:34][S:30][CH:31]=3)[CH:15]=[CH:14][C:13]=2[N:12]1[S:16]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)(=[O:17])=[O:18])[CH3:28]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 581760Thiophene-3-boronic acidHCID 224823412-Bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

Product 1

HCID 22482332HCID 22482332, compoundYield 51.4%

Reagents, catalysts & solvents 1

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

Procedure

The title compound was prepared from 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (Example 44, Step c, 0.35 g, 0.73 mmol), 3-thiopheneboronic acid (0.09 g, 0.73 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.02 g, 0.02 mmol), and a 5 N aqueous sodium hydroxide solution (0.3 mL, 1.5 mmol) according to the procedure and in the same manner as described in Example 47, Step a. The crude material was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4) to yield 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-thien-3-yl-5,6-dihydrophenanthridine as a solid (0.18 g, 51%);

Workup

  1. customThe crude material was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-84a77b5d7397499d8d320a6cb52c03ff
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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