(4-Fluoro-2-methoxyphenyl)boronic acid → 4-(4-fluoro-2-methoxyphenyl)-N-(3-nitrophenyl)pyridin-2-amine

HRID 593283Notes

Reaction equation

HRID 593283 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[C:21]([O:28][CH3:29])[CH:20]=1.ClC1C=C(C2C=CC(F)=CC=2OC)C=CN=1>>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=3)[CH:3]=2)=[C:21]([O:28][CH3:29])[CH:20]=1

Participants

4

Reactant 3

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 584326092-Chloro-4-(4-fluoro-2-methoxyphenyl)pyridineHCID 682872994-iodo-N-(3-nitrophenyl)pyridine-2-amine

Product 1

HCID 601965424-(4-fluoro-2-methoxyphenyl)-N-(3-nitrophenyl)pyridin-2-amineYield 80.2%

Procedure

The title compound C2 was prepared from A5 (122 mg, 0.36 mmol) and (4-fluoro-2-methoxyphenyl)boronic acid (112 mg, 0.66 mmol) following the procedure reported for the intermediate A2. The residue was purified by flash chromatography on silica gel (cHex/EtOAc 100:0 to 50:50) to yield the desired product C2 as an orange solid (98 mg, 80%). MS (ES) C18H14FN3O3 requires: 339. found: 340 (M+H)+.

Workup

  1. customThe residue was purified by flash chromatography on silica gel (cHex/EtOAc 100:0 to 50:50)

Sources & evidence

ORD record
ord-b997eeaaad224058af08c227227aca40
Source dataset
uspto-grants-2016_01
Patent number
US09242937B2

Reaction notes

Loading…