1-(2,6-Dichlorophenyl)ethanol → 3-Bromo-7-[1-(2,6-dichlorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine
Reaction equation
BrC1C2C=NC([N+]([O-])=O)=C(O)C=2OC=1.ClC1C=CC=C(Cl)C=1C(O)C.ClC1C(F)=CC=C(Cl)C=1[C@H](OC1C2OC=CC=2C=NC=1[N+]([O-])=O)C.[Br:50][C:51]1[C:55]2[CH:56]=[N:57][C:58]([N+:71]([O-])=O)=[C:59]([O:60][CH:61]([C:63]3[C:68]([Cl:69])=[CH:67][CH:66]=[CH:65][C:64]=3[Cl:70])[CH3:62])[C:54]=2[O:53][CH:52]=1>[Fe].Cl>[Br:50][C:51]1[C:55]2[CH:56]=[N:57][C:58]([NH2:71])=[C:59]([O:60][CH:61]([C:63]3[C:64]([Cl:70])=[CH:65][CH:66]=[CH:67][C:68]=3[Cl:69])[CH3:62])[C:54]=2[O:53][CH:52]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Bromo-6-nitrofuro[3,2-c]pyridin-7-ol (Intermediate 10) was reacted with racemic 1-(2,6-dichlorophenyl)ethanol following the procedure described for Intermediate 8. The resulting 3-Bromo-7-[1-(2,6-dichlorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine was reacted with iron/HCl as described in Example 2 to give 3-Bromo-7-[1-(2,6-dichlorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine. Suzuki coupling with 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester and Boc removal with HCl as described for Example 333 gave the title compound as HCl salt. 1H NMR (400 MHz, CD3OD): δ=1.86 (d, J=6.8 Hz, 3H), 1.91-2.03 (m, 2H), 2.11 (dd, J=12.0, 2.2 Hz, 2H), 2.75 (td, J=12.8, 2.5 Hz, 2H), 3.13-3.23 (m, 2H), 4.26-4.39 (m, 1H), 6.59 (q, J=6.8 Hz, 1H), 7.23 (d, J=7.8 Hz, 1H), 7.31-7.39 (m, 2H), 7.77 (s, 1H), 7.82 (s, 1H), 8.07 (s, 1H), 8.13 (s, 1H). MS (ES+): m/z 472.00/474.00 [MH+]. HPLC: tR=2.38 min (ZQ3, polar—5 min).
Sources & evidence
- ORD record
- ord-021578e704f1465e830f0513872d21c3
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022206B2
Reaction notes
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