Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181848Notes

Reaction equation

HRID 2181848 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10](=[C:11]3[C:16]=1[CH:15]=[C:14]([F:17])[CH:13]=[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.[Cl:48][C:49]1[CH:50]=[C:51]([S:57](Cl)(=[O:59])=[O:58])[CH:52]=[CH:53][C:54]=1[O:55][CH3:56]>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][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:57]([C:51]1[CH:52]=[CH:53][C:54]([O:55][CH3:56])=[C:49]([Cl:48])[CH:50]=1)(=[O:58])=[O:59])[CH3:2]

Participants

10

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chlorideHCID 22482260HCID 22482260, compound

Product 2

HCID 2199665,6-DihydrophenanthridineHCID 22482342HCID 22482342, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The intermediate dihydrophenanthridine was prepared from 6-ethyl-8-fluorophenanthridine, (Example 40, Step b, 0.40 g, 1.8 mmol), by treatment with sodium borohydride (0.40 g, 10.6 mmol) and trifluoroacetic acid (0.55 mL, 7.1 mmol) in tetrahydrofuran (7 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (0.9 mL, 6.4 mmol) and 3-chloro-4-methoxybenzenesulfonyl chloride (0.51 g, 2.1 mmol, 2.1 equivalents) in dichloromethane (5 mL), according to the procedure and in the same manner as described in Example 32, Method A, Step d, to afford 6-ethyl-8-fluoro-5-[(3-chloro-4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine as a crude product, which was utilized without further purification.

Sources & evidence

ORD record
ord-1afc60d4b4184dada63199b24b44fd26
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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