HCID 14810917, compound → HCID 136404511, compound

HRID 1710105Notes

Reaction equation

HRID 1710105 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-bromoacetylpyridinium 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 (3H, s, NCH3), 7.2-7.4 (2H, m, H-5 and H-6), 7.58 (1H, d, J=7.4 Hz, H-7), 8.03 (1H, dd, J=5.5, 8.1 Hz, H-5" β-pyr), 8.26 (1H, s, H-5' thiazole), 8.36 (1H, d, partially buried, H-4), 8.38 (1H, s, H-2), 8.83 (1H, mc, H-4" γ-pyr), 8.99 (1H, d, J=8.2 Hz, H-6" α-pyr), 9.47 (1H, mc, H-2" α-pyr); m/z 291 (M+, 100%), 135 (30).

Sources & evidence

ORD record
ord-f0250c0aeb4742409268978fd859e2ba
Source dataset
uspto-grants-1990_08
Patent number
US04952587

Reaction notes

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