5-Bromoindole-3-carbaldehyde → HCID 4186285, compound

HRID 402303Notes

Reaction equation

HRID 402303 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[O:12].[C:13]1([CH3:22])[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1>>[C:13]1([CH3:22])[CH:18]=[CH:17][CH:16]=[C:15]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:11]=[O:12])[CH:14]=1

Participants

3

Reactant 2

HCID 701375-Bromoindole-3-carbaldehydeHCID 27339503-Tolylboronic acid

Product 1

HCID 4186285HCID 4186285, compoundYield 85%

Procedure

5-Bromo-1H-indole-3-carbaldehye was reacted with m-tolylboronic acid as described for 3-6 and 3-7. Yield: 85%; 1H NMR (300 MHz, CDCl3): δ 9.91 (s, 1 H), 8.43 (s, 1 H), 7.66 (s, 1 H), 7.36 (d, J=7.5 Hz, 1 H), 7.20 (d, J=8.7, 1 H), 4.11 (t, J=7.2 Hz, 2 H), 1.85 (t, J=6.3 Hz, 2 H), 1.30-1.24 (m, 10 H), 0.86 (t, J=6 Hz, 3 H); 13C NMR (75 MHz, CDCl3): δ 184.1, 138.7, 135.8, 126.8, 126.8, 124.7, 117.3, 116.4, 111.4, 47.4, 32.7, 31.6, 29.6, 29.0, 26.7, 22.5, 14.0.

Sources & evidence

ORD record
ord-e9f0221df8284d858b7b0377418ebdb5
Source dataset
uspto-grants-2014_06
Patent number
US08742100B2

Reaction notes

Loading…