Carbon Dioxide → HCID 86689249, compound

HRID 1409509Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][C:18]=4[C:17]([NH2:24])=[N:16]3)[C:14]3[CH:13]=[C:12]([Cl:25])[N:11]=[C:10]([F:26])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.C(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C@:15]3([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][C:18]=4[C:17]([NH2:24])=[N:16]3)[C:14]3[CH:13]=[C:12]([Cl:25])[N:11]=[C:10]([F:26])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 280Carbon Dioxide

HCID 88586770HCID 88586770, compound

Product 1

HCID 86689249HCID 86689249, compound

Procedure

7-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,3′-pyrrolo[3,4-c]pyridin]-1′-amine (483 mg) was subjected to chromatography using supercritical CO2 (additives 35% MeOH with 20 mM NH3) on a ChiralPak ADH (21×250 mm, 5 μm) eluting at a flow rate 65 ml/min (100 bar pressure, 40° C. column temperature). The first peak (retention time=1.8 min) provided (R)-7-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,3′-pyrrolo[3,4-c]pyridin]-1′-amine (Example 14c-1, >99% ee), and the second peak (retention time=3.5 min) provided (S)-7-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,3′-pyrrolo[3,4-c]pyridin]-1′-amine (Example 14c-2, >99% ee).

Workup

washeluting at a flow rate 65 ml/min (100 bar pressure, 40° C. column temperature)

Sources & evidence

ORD record: ord-3405715b2c5a4d729cb3ecd0a798e491
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921363B2

Reaction notes

Loading…