Carbon Dioxide → HCID 86689256, compound

HRID 1409516Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([C:23]4[C:18](=[N:19][CH:20]=[CH:21][CH:22]=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:23]4[C:18](=[N:19][CH:20]=[CH:21][CH:22]=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 86689253HCID 86689253, compound

Product 1

HCID 86689256HCID 86689256, compound

Procedure

7-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,5′-pyrrolo[3,4-b]pyridin]-7′-amine subjected to chromatography using supercritical CO2 (additives 50% MeOH with 20 mM NH3) on a Chiralpak ADH column (21×250 mm, 5 μm) eluting at a flow rate 63 ml/min (100 bar pressure, 40° C. column temperature). The first peak (retention time=2.34 min) provided (R)-7-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,5′-pyrrolo[3,4-b]pyridin]-7′-amine (Example 17c-1; 99% ee), and the second peak (retention time=3.98 min) provided (S)-7-Bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,5′-pyrrolo[3,4-b]pyridin]-7′-amine (Example 17c-2; 99% ee).

Workup

washeluting at a flow rate 63 ml/min (100 bar pressure, 40° C. column temperature)

Sources & evidence

ORD record: ord-7b03a38682ea4e14bb91768879314454
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921363B2

Reaction notes

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