1-methyl-1H-indol-5-amine → HCID 59318066, compound

HRID 2190533Notes

Reaction equation

HRID 2190533 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7](N)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.ClC1C=CC(C(Cl)=O)=CN=1.[Cl:22][C:23]1[CH:39]=[CH:38][C:26]([C:27]([NH:29]C2C=CC(I)=C(C)C=2)=[O:28])=[CH:25][N:24]=1>>[Cl:22][C:23]1[CH:39]=[CH:38][C:26]([C:27]([NH:29][C:8]2[CH:9]=[C:10]3[C:5]([CH:4]=[CH:3][N:2]3[CH3:1])=[CH:6][CH:7]=2)=[O:28])=[CH:25][N:24]=1

Participants

4

Reactant 3

HCID 27695641-methyl-1H-indol-5-amineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 59318066HCID 59318066, compound

Procedure

6-Chloro-N-(1-methyl-1H-indol-6-yl)-nicotinamide was prepared from 1-methyl-1H-indol-5-ylamine (prepared as described in J. Med. Chem. 2007, 5509) and 6-chloronicotinoyl chloride in a manner similar to the one described in the synthesis of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide, above. The product was isolated after purification with a silica gel column and 0.0-30% EtOAc in hexanes gradient. H1 NMR (300 MHz, chloroform-d) d ppm 3.79 (s, 3H), 6.44 (d, J=3.0 Hz, 1H), 6.94 (dd, J=10.2, 8.4 Hz 1H), 7.04 (d, J=3.0, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.89 (s, 1H), 8.05 (s, 1H), 8.16 (dd, J=10.2, 8.4 Hz, 1H), 8.87 (apparent s, 1H)

Workup

  1. customThe product was isolated
  2. customafter purification with a silica gel column and 0.0-30% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-49a747aebcb94dcc8e6938a262a6379f
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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