HCID 14810917, compound → HCID 136404511, compound

HRID 2248603Notes

Reaction equation

HRID 2248603 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[S:13])[NH2:12])=[CH:3]1.Br.[Br:15][CH2:16][C:17]([C:19]1[CH:20]=[NH+:21][CH:22]=[CH:23][CH:24]=1)=O>CN(C=O)C>[BrH:15].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[S:13][CH:16]=[C:17]([C:19]3[CH:20]=[NH+:21][CH:22]=[CH:23][CH:24]=3)[N:12]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 14810917HCID 14810917, compoundHCID 18984598HCID 18984598, compound

Product 1

HCID 136404511HCID 136404511, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Methylindole-3-thiocarboxamide (0.5 g) was dissolved in anhydrous DMF (5 ml). This solution was added to a stirred suspension of 3-bromoacetyl-pyridinium hydrobromide (1.1 g) in anhydrous DMF (2 ml). This was stirred for 10 minutes at room temperature. The title compound was isolated by filtration and was washed thoroughly with ether, 0.5 g. δH (360 MHz, DMSO-d6) 3.91 (3 H, s, NCH3), 7.2-7.4 (2 H, m, H-5 and H-6), 7.58 (1 H, d, J=7.4 Hz, H-7) 8.03 (1 H, dd, J=5.5, 8.1 Hz, H-5" β pyr), 8.26 (1 H, s, H-5' thiazole), 8.36 (1H, d, partially buried, H-4), 8.38 (1 H, s, H-2), 8.83 (1 H, mc, H-4" γ pyr), 8.99 (1 H, d, J=8.2 Hz, H-6" α-pyr), 9.47 (1 H, mc, H-2" α-pyr); m/z 291 (M+, 100%), 135 (30).

Sources & evidence

ORD record
ord-c181ec00466548c28c60119f07d8bd4a
Source dataset
uspto-grants-1991_08
Patent number
US05041456

Reaction notes

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