Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181855Notes

Reaction equation

HRID 2181855 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([CH3:16])[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[F:47][C:48]1[CH:49]=[C:50]([S:56](Cl)(=[O:58])=[O:57])[CH:51]=[CH:52][C:53]=1[O:54][CH3:55]>O1CCCC1.ClCCl>[CH:2]1[CH:15]=[CH:14][C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][CH2:5][C:4]=2[CH:3]=1.[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:56]([C:50]1[CH:51]=[CH:52][C:53]([O:54][CH3:55])=[C:48]([F:47])[CH:49]=1)(=[O:57])=[O:58])[CH:5]2[CH3:16]

Participants

10

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 27745403-Fluoro-4-methoxybenzene-1-sulfonyl chlorideHCID 4311764Sodium borohydrideHCID 224823738-Fluoro-6-methylphenanthridine

Product 2

HCID 2199665,6-DihydrophenanthridineHCID 224822898-Fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The intermediate dihydrophenanthridine was prepared from 8-fluoro-6-methylphenanthridine, (Example 32, Method A, Step b, 2.00 g, 9.45 mmol), by treatment with sodium borohydride (1.79 g, 47.4 mmol) and trifluoroacetic acid (2.9 mL, 37.9 mmol) in tetrahydrofuran (38 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (2.7 mL, 19 mmol) and 3-fluoro-4-methoxybenzenesulfonyl chloride (0.78 g, 3.5 mmol, 1.1 equivalents) in dichloromethane (5 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 8-fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine as a homogeneous solid (1.08 g, 84% from the dihydrophenanthridine), m.p. 146-147° C.;

Workup

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

Sources & evidence

ORD record
ord-d2d6e18ff5384c21be8b2410b19f82de
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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