4-Formylphenylboronic Acid → 4-[7-(1H-Indol-5-ylamino)-thieno[3,2-b]pyridin-2-yl]-benzaldehyde

HRID 2297796Notes

Reaction equation

HRID 2297796 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[S:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][C:19]=2[NH:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][CH:27]=[CH:26]3)[CH:14]=1>>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([NH:22][C:19]3[CH:18]=[CH:17][N:16]=[C:15]4[CH:14]=[C:13]([C:6]5[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=5)[S:21][C:20]=34)=[CH:31][CH:30]=2)[CH:26]=[CH:27]1

Participants

3

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 18382766(2-bromo-thieno[3,2-b]pyridin-7-yl)-(1H-indol-5-yl)-amine

Product 1

HCID 183827434-[7-(1H-Indol-5-ylamino)-thieno[3,2-b]pyridin-2-yl]-benzaldehyde

Procedure

The title compound was prepared from 4-formylbenzeneboronic acid and (2-bromo-thieno[3,2-b]pyridin-7-yl)-(1H-indol-5-yl)-amine by a procedure analogous to example 17. 1H NMR (400 MHz, DMSO) d 11.1 (s, 1H), 9.98 (s, 1H), 8.21 (d, 1H), 8.05 (s, 1H), 7.95 (s, 3H), 7.82 (d, 1H), 7.60 (m, 3H), 7.00 (d, 1H), 6.58 (s, 1H), 6.40 (s, 1H), LC-MS: 370 (MH+); HPLC RT: 4.83 minutes.

Sources & evidence

ORD record
ord-ee43572729ed4a1c887463d9ef5a058f
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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