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

HRID 751405Notes

Reaction equation

HRID 751405 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.[CH:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)=[CH2:14]>>[Cl:1][C:2]1[N:3]([C:18]2[CH:19]=[CH:20][C:15]([CH:13]=[CH2:14])=[CH:16][CH:17]=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 27343934-Vinylphenylboronic acid

Product 1

HCID 860359372-chloro-1-(4-vinylphenyl)-1H-indole-3-carboxaldehydeYield 28%

Procedure

2-Chloro-1H-indole-3-carboxaldehyde is reacted with 4-vinylphenylboronic acid as described in step-1 of Example 29 to afford 2-chloro-1-(4-vinylphenyl)-1H-indole-3-carboxaldehyde (28% yield) as a off white solid. ESI/MS 282 (M+H); RT 3.59 min; NMR 10.22 (1H, s); 8.36 (1H, d, J=6 Hz); 7.65 (2H, d); 7.37 (5H, m); 6.87 (1H, dd); 5.92 (1H, d, J=18 Hz); 5.45 (1H, d, J=12 Hz).

Sources & evidence

ORD record
ord-05c97a0daaa64ec698e85105e65ed172
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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