3-(2,4-Bis-trifluoromethyl-phenyl)-6-chloromethyl-pyridazine → 2-[6-(2,4-Bis-trifluoromethylphenyl)-pyridazin-3-ylmethyl]-6-(2-fluorophenyl)-2H-pyrrolo[2,3-c]pyridazine

HRID 2408483Notes

Reaction equation

HRID 2408483 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:16][C:11]2[N:12]=[N:13][CH:14]=[CH:15][C:10]=2[CH:9]=1.[F:17][C:18]([F:38])([F:37])[C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[C:29]1[N:30]=[N:31][C:32]([CH2:35]Cl)=[CH:33][CH:34]=1>>[F:38][C:18]([F:17])([F:37])[C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:22]=[CH:21][C:20]=1[C:29]1[N:30]=[N:31][C:32]([CH2:35][N:13]2[CH:14]=[CH:15][C:10]3=[CH:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[N:16][C:11]3=[N:12]2)=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 249967593-(2,4-Bis-trifluoromethyl-phenyl)-6-chloromethyl-pyridazineHCID 674703746-(2-fluorophenyl)-7H-pyrrolo[2,3-c]pyridazine

Product 1

HCID 547599532-[6-(2,4-Bis-trifluoromethylphenyl)-pyridazin-3-ylmethyl]-6-(2-fluorophenyl)-2H-pyrrolo[2,3-c]pyridazineYield 18%

Procedure

Prepared analogously to the method described for 2-[5[(4-methoxy-2-trifluoro-methylphenyl)-[1,3,4]thiadiazol-2-ylmethyl]-6-(2-fluorophenyl)-2H-pyrrolo[2,3-c]pyridazine beginning with 6-(2-fluorophenyl)-7H-pyrrolo[2,3-c]pyridazine (50 mg, 0.234 mmol) and 3-(2,4-Bis-trifluoromethylphenyl)-6-chloromethylpyridazine (95 mg, 0.27 mmol) to produce the titled compound (21.6 mg, 18%). 1H-NMR: (d6-DMSO, 400 MHz) δ 8.78 (d, 1H), 8.38 (dt, 1H), 8.21 (d, 2H), 8.02 (d, 1H), 7.95 (d, 1H), 7.89 (d, 1H), 7.86 (d, 1H), 7.47 (m, 1H), 7.31 (m, 2H), 7.12 (d, 1H), 6.22 (s, 2H). LCMS calculated for C25H14F7N5: 517.11, found 518.15 (M+H)+.

Workup

  1. customPrepared analogously to the method

Sources & evidence

ORD record
ord-bd1b473cae8444dba6c8147788a92aa4
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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