Hydroxylamine → CH 150

HRID 550888Notes

Reaction equation

HRID 550888 reaction equation
[NH:1]1C2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[C:3](C=O)=[CH:2]1.FC1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.N1C=NN=N1.[N-]=[N+]=[N-].[Na+].N[OH:31]>>[CH3:20][CH2:19][C:16]1[C:17](=[O:31])[N:18]2[C:2]([CH:3]=[CH:4][CH:5]=[C:6]2[CH3:7])=[N:1][C:15]=1[CH3:14]

Participants

6

Reactant 5

HCID 787HydroxylamineHCID 10256Indole-3-CarboxaldehydeHCID 145174-FluorobenzonitrileHCID 33557Sodium AzideHCID 178418441HCID 178418441, compound

Product 1

HCID 93406CH 150

Procedure

XO-CH145 was prepared by coupling of indole-3-carboaldehyde and 4-fluorobenzonitrile in a similar manner to the third step of the above 1. XO-CH147 was prepared by converting XO-CH145 into a tetrazole derivative using sodium azide, followed by cyanation using hydroxylamine to give XO-CH150 (the following scheme).

Workup

  1. customXO-CH147 was prepared

Sources & evidence

ORD record
ord-cbc315a9f0e844ab8f7c0c93a6e62a53
Source dataset
uspto-grants-2011_05
Patent number
US07947707B2

Reaction notes

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