6-(2-fluorophenyl)-7H-pyrrolo[2,3-c]pyridazine → 2-[3-(2,4-Bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl]-6-(2-fluorophenyl)-2H-pyrrolo[2,3-c]pyridazine

HRID 2408482Notes

Reaction equation

HRID 2408482 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:47])([F:46])[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[CH:33]=[C:32]([CH2:34]OS(C2C=CC(C)=CC=2)(=O)=O)[O:31][N:30]=1>>[F:47][C:18]([F:17])([F:46])[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[CH:33]=[C:32]([CH2:34][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)[O:31][N:30]=1

Participants

3

Reactant 2

HCID 674703746-(2-fluorophenyl)-7H-pyrrolo[2,3-c]pyridazineHCID 86688863Toluene-4-sulfonic acid 3-(2,4-bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl ester

Product 1

HCID 547597682-[3-(2,4-Bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl]-6-(2-fluorophenyl)-2H-pyrrolo[2,3-c]pyridazineYield 21.1%

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 toluene-4-sulfonic acid 3-(2,4-bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl ester (164 mg, 0.35 mmol) to produce the titled product (25 mg, 21%). 1H-NMR: (d6-DMSO, 400 MHz) δ 8.73 (d, 1H), 8.40 (dt, 1H), 8.21 (d, 1H), 8.16 (d, 1H), 8.04 (d, 2H), 7.93 (d, 1H), 7.48 (m, 1H), 7.32 (m, 2H), 7.14 (d, 1H), 7.00 (s, 1H), 6.15 (s, 2H). LCMS calculated for C24H13F7N4O 506.10, found 507.07 (M+H)+.

Workup

  1. customPrepared analogously to the method

Sources & evidence

ORD record
ord-00cee53f70e3404fb6792359d9804101
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

Loading…