Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181840Notes

Reaction equation

HRID 2181840 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10](=[C:11]3[C:16]=1[CH:15]=[CH:14][C:13]([CH3:17])=[CH:12]3)[CH:9]=[CH:8][CH:7]=[CH:6]2)[CH3:2].[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[CH3:48][O:49][C:50]1[CH:55]=[CH:54][C:53]([S:56](Cl)(=[O:58])=[O:57])=[CH:52][CH:51]=1>O1CCCC1.ClCCl>[CH:14]1[CH:13]=[CH:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[NH:4][CH2:3][C:16]=2[CH:15]=1.[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:56]([C:53]1[CH:52]=[CH:51][C:50]([O:49][CH3:48])=[CH:55][CH:54]=1)(=[O:58])=[O:57])[CH3:2]

Participants

10

Reactant 6

HCID 6422Trifluoroacetic acidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 22482261HCID 22482261, compound

Product 2

HCID 2199665,6-DihydrophenanthridineHCID 22482343HCID 22482343, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The intermediate dihydrophenanthridine was prepared from 6-ethyl-9-methylphenanthridine, (Example 42, Step b, 0.50 g, 2.3 mmol), by treatement with sodium borohydride (0.51 g, 13.5 mmol) and trifluoroacetic acid (0.7 mL, 9 mmol) in tetrahydrofuran (11 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (1.9 mL, 14 mmol) and 4-methoxybenzenesulfonyl chloride (0.93 g, 4.50 mmol) in dichloromethane (11 mL) according to the procedure and in the same manner as described in Example 32, Method A, Step d. The crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane to yield 6-ethyl-5-[(4-methoxyphenyl)sulfonyl]-9-methyl-5,6-dihydrophenanthridine as a homogeneous, white, crystalline, solid, m.p. 133° C.;

Workup

  1. customThe crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-9db5aa9723ae4b1b8c4bb86055a001f7
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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