Thiophene-3-boronic acid → (1H-Indol-5-yl)-(6-thiophen-3-yl-thieno[3,2-d]pyrimidin-4-yl)-amine

HRID 2297760Notes

Reaction equation

HRID 2297760 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[S:18][C:17]2[C:16]([NH:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)=[N:15][CH:14]=[N:13][C:12]=2[CH:11]=1>>[NH:25]1[C:26]2[C:22](=[CH:21][C:20]([NH:19][C:16]3[C:17]4[S:18][C:10]([C:3]5[CH:4]=[CH:5][S:1][CH:2]=5)=[CH:11][C:12]=4[N:13]=[CH:14][N:15]=3)=[CH:28][CH:27]=2)[CH:23]=[CH:24]1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 18383051(6-Bromo-thieno[3,2-d]pyrimidin-4-yl)-(1H-indol-5-yl)-amine

Product 1

HCID 18383059(1H-Indol-5-yl)-(6-thiophen-3-yl-thieno[3,2-d]pyrimidin-4-yl)-amine

Procedure

The title compound was prepared from thiophene-3-boronic acid and (6-bromo-thieno[3,2-d]pyrimidin-4-yl)-(1H-indol-5-yl)-amine by a procedure analogous to example 2. 1H NMR (400 MHz, DMSO) d 11.4 (s, 1H), 11.2 (s, 1H), 8.86 (s, 1H), 8.10 (s, 1H), 7.70 (m, 3H), 7.46 (m, 3H), 7.21 (d, 1H), 6.49 (s, 1H), M.P. 178-189° C.; LC-MS: 349 (MH+); HPLC RT 4.05 minutes.

Sources & evidence

ORD record
ord-a3300f3e785845cda5d817abcf43ee56
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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