Ethanol → Quinoline-5-carbaldehyde

HRID 2243312Notes

Reaction equation

HRID 2243312 reaction equation
[N:1]1C2C=CN=CC=2N[C:2]=1[C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15](N)C=2C=CC=1.C([OH:26])C>>[N:1]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:15]=[O:26])[C:21]=2[CH:22]=[CH:10][CH:2]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 56594091HCID 56594091, compound

Product 1

HCID 3543386Quinoline-5-carbaldehyde

Procedure

Carry out the procedure as in Example 18, starting from 100 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluorene-9(R,S)-amine, obtained in Example 6, and 59 mg of quinoline-5-carboxaldehyde in 1 ml of ethanol for 3 hours at room temperature, then add 29 mg of sodium hydroborate and stir for 2 hours at room temperature. After purification by HPLC/MS on a Symmetry C18 silica column (5 μm), eluting with a gradient of water 100% (containing 0.07% of TFA) to acetonitrile 100% (containing 0.07% of TFA), we obtain 49.5 mg of trifluoroacetate of N-[4-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-fluoren-9(R,S)-yl]-quinolin-5-yl-methylamine, in the form of a pale yellow solid with the following characteristics:

Sources & evidence

ORD record
ord-bb8cd715c6614cef8de1df33af490c2d
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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