5-Bromo-2-chloroisonicotinic acid → 8-Chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepine

HRID 2401416Notes

Reaction equation

HRID 2401416 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:22]([CH3:23])=[N:21][O:20][C:7]=3[CH2:8][N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[C:11]=2[N:12]=1.BrC1C(C(O)=O)=CC(Cl)=NC=1.BrC1C(C(O)=O)=NC(Cl)=CC=1>>[Cl:1][C:2]1[N:12]=[CH:11][C:5]2[C:6]3[C:22]([CH3:23])=[N:21][O:20][C:7]=3[CH2:8][N:9]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 201379075-Bromo-2-chloroisonicotinic acidHCID 269667323-Bromo-6-chloropyridine-2-carboxylic acidHCID 866667278-Chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepine2×

Product 1

HCID 866667288-Chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepine

Procedure

A sequence similar to 8-chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepine (Compound 240) was followed, except that 5-bromo-2-chloroisonicotinic acid was used as commercially available starting material instead of 3-bromo-6-chloropicolinic acid. LC/MS m/z 344 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.93 (d, J=0.80 Hz, 1H), 7.49 (td, J=2.10, 8.70 Hz, 2H), 7.46-7.42 (m, 3H), 4.77 (br. s, 2H), 2.57 (s, 3H).

Sources & evidence

ORD record
ord-9ef06b241a8e4363bacbcd1e890537bd
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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