4-Bromobenzoyl chloride → HCID 70982294, compound

To a stirred solution of 6-(2-benzyloxy-ethoxy)-1H-indazol-3-ylamine (3.0 g, 10.6 mmol) in 30 ml of dry pyridine, at 0° C., under argon atmosphere, was added portionwise 4-bromo-benzoyl chloride (2.32 g, 10.6 mmol). The reaction mixture was allowed to warm to r.t. under stirring overnight then evaporated to dryness. The residue was treated with 50 ml of MeOH and 25 ml of 2N NaOH and stirred at r.t. for 1 h. The mixture was concentrated to ca. 10 ml by rotary evaporation, diluted with 200 ml of water, stirred for 15 min at r.t. and the suspended solid filtered and washed with water. After drying under vacuum, the crude solid was purified by chromatography (Biotage SP1 Flash Purification system) on a silica gel cartridge (Biotage SNAP 100 g) using DCM as eluant A and DCM/MeOH 9:1 as eluant B. Elution with a gradient from A/B 100:0 to 70:30 over 25 CV gave a pink solid that was triturated with EtOAc (50 ml), filtered, washed with EtOAc and dried affording 3.01 g (yield: 61%) of the title compound as a whitish solid.

1. customthen evaporated to dryness
2. additionThe residue was treated with 50 ml of MeOH and 25 ml of 2N NaOH
3. stirringstirred at r.t. for 1 h
4. concentrationThe mixture was concentrated to ca. 10 ml by rotary evaporation
5. additiondiluted with 200 ml of water
6. stirringstirred for 15 min at r.t.
7. filtrationthe suspended solid filtered
8. washwashed with water
9. customAfter drying under vacuum
10. customthe crude solid was purified by chromatography (Biotage SP1 Flash Purification system) on a silica gel cartridge (Biotage SNAP 100 g)
11. washElution with a gradient from A/B 100:0 to 70:30 over 25 CV
12. customgave a pink solid
13. customthat was triturated with EtOAc (50 ml)
14. filtrationfiltered
15. washwashed with EtOAc
16. customdried

ORD record

ord-e424ae61d68e49338d9aae7602832aed

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09408850B2