2-chloro-1H-indole-3-carbaldehyde → 2-chloro-1-(4-methyl-3-nitrophenyl)-1H-indole-3-carboxaldehyde

HRID 1678177Notes

Reaction equation

HRID 1678177 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]>>[Cl:1][C:2]1[N:3]([C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[C:15]([N+:23]([O-:25])=[O:24])[CH:16]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

3

Reactant 2

HCID 3147912-chloro-1H-indole-3-carbaldehydeHCID 27735154-Methyl-3-nitrobenzeneboronic acid

Product 1

HCID 860359152-chloro-1-(4-methyl-3-nitrophenyl)-1H-indole-3-carboxaldehydeYield 35%

Procedure

2-Chloro-1H-indole-3-carboxaldehyde is reacted with 4-methyl-3-nitrophenylboronic acid as described in Step 1 of Example 29 to afford 2-chloro-1-(4-methyl-3-nitrophenyl)-1H-indole-3-carboxaldehyde (35% yield) as a light cream solid. ESI/MS 315 (M+H); 356 [(M+1+CH3CN) adduct]; RT=3.35 min.

Sources & evidence

ORD record
ord-49926f27ee9d40248546cc3e23ad3f4f
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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