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

HRID 751390Notes

Reaction equation

HRID 751390 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.[CH2:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)[CH3:14]>>[Cl:1][C:2]1[N:3]([C:18]2[CH:19]=[CH:20][C:15]([CH2:13][CH3:14])=[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 2734352Boronic acid, (4-ethylphenyl)-

Product 1

HCID 860359032-Chloro-1-(4-ethylphenyl)-1H-indole-3-carboxaldehydeYield 73%

Procedure

2-Chloro-1H-indole-3-carboxaldehyde is reacted with 4-ethylphenylboronic acid as described in Step 1 of Example 29 to afford 2-chloro-1-(4-ethyl-phenyl)-1H-indole-3-carboxaldehyde (73% yield) as a light yellow solid. ESI/MS 284 (M+H); RT 4.04 min; NMR 10.12 (1H, s); 8.20 (1H, d, J=9 Hz); 7.54 (4H, m); 7.38 (2H, m); 7.28 (1H, d); 2.77 (2H, q); 1.28 (3H, t).

Sources & evidence

ORD record
ord-f470f7afb385444987ded21192dde74c
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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