Riboflavin → 5-(6-amino-1-isopropyl-1H-indol-3-yl)-pyridine-2-carbonitrile

HRID 2079883

Reaction equation

HRID 2079883 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[C:6]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=C[CH:17]=2)=[CH:5]1)([CH3:3])[CH3:2].[NH2:24]C1C=C2C(C(C3C=CC(C#N)=CC=3)=CN2C(C)C)=CC=1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>[Pd].[Pt]=O>[NH2:13][C:10]1[CH:11]=[C:12]2[C:7]([C:6]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[N:24][CH:17]=3)=[CH:5][N:4]2[CH:1]([CH3:3])[CH3:2])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 493570RiboflavinHCID 574421944-(1-isopropyl-6-nitro-1H-indol-3-yl)-benzonitrileHCID 574422014-(6-amino-1-isopropyl-1H-indol-3-yl)-benzonitrile

Product 1

HCID 671011895-(6-amino-1-isopropyl-1H-indol-3-yl)-pyridine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)Catalyst

Procedure

Method F This compound can be prepared from 5-(1-isopropyl-6-nitro-1H-indol-3-yl)-pyridine-2-carbonitrile (4, R1=i-Pr, R3=5-(2-cyanopyridine)) in a manner substantially similar to that described immediately above for 4-(6-amino-1-isopropyl-1H-indol-3-yl)-benzonitrile except Degussa type E101 NE/W 10% Palladium on activated carbon can be used instead of platinum (II) oxide in Method E. LRMS (API ES+)=277.0 (M+H).

Sources & evidence

ORD record
ord-06449a27ab5444758edff0c311d6740c
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Linked notes

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