3-Aminopyridine → HCID 50994029, compound

HRID 1784818Notes

Reaction equation

HRID 1784818 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1.N1C2C(=C(C3C=C(NC4C=NC=CC=4)C=C(OC)C=3)C=CC=2)C=C1>>[Br:10][C:4]1[CH:3]=[C:2]([NH:17][C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

Participants

4

Reactant 3

HCID 100093-AminopyridineHCID 110218123,5-DibromoanisoleHCID 15604425HCID 15604425, compound

Product 1

HCID 50994029HCID 50994029, compound

Procedure

(3-Bromo-5-methoxy-phenyl)-pyridin-3-yl-amine was prepared from 1,3-dibromo-5-methoxy-benzene and pyridin-3-ylamine as described for Example 36. This material was converted to [3-(1H-indol-4-yl)-5-methoxy-phenyl]-pyridin-3-yl-amine by the method of Example 35. 1H NMR (400 MHz, CDCl3): δ 8.44 (d, J=2.7 Hz, 1H), 8.34 (br s, 1H), 8.17 (dd, J=4.7, 1.2 Hz, 1H), 7.50 (ddd, J=8.2, 2.7, 1.4 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 7.27-7.23 (m, 2H), 7.19-7.15 (m, 2H), 6.98 (t, J=1.7 Hz, 1H), 6.89 (dd, J=2.2, 1.4 Hz, 1H), 6.73 (t, J=2.1 Hz, 1H), 6.64 (t, J=2.2 Hz, 1H), 5.81 (s, 1H), 3.84 (s, 3H).

Sources & evidence

ORD record
ord-d5753192d0224faa86d0e163bf369cc3
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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