2-Ethylpyridin-3-amine → (3-Bromo-5-triisopropylsilanyloxy-phenyl)-(2-ethyl-pyridin-3-yl)-amine

HRID 1784879Notes

Reaction equation

HRID 1784879 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Br:19])[CH:18]=1)[O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].[CH2:20]([C:22]1[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][N:23]=1)[CH3:21]>>[Br:19][C:17]1[CH:18]=[C:2]([NH:28][C:27]2[C:22]([CH2:20][CH3:21])=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:3]=[C:4]([O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])[CH:16]=1

Participants

3

Reactant 2

HCID 218818002-Ethylpyridin-3-amineHCID 50994104(3,5-Dibromo-phenoxy)-triisopropyl-silane

Product 1

HCID 68842636(3-Bromo-5-triisopropylsilanyloxy-phenyl)-(2-ethyl-pyridin-3-yl)-amine

Procedure

(3,5-Dibromo-phenoxy)-triisopropyl-silane and 2-ethyl-pyridin-3-ylamine were coupled to give (3-bromo-5-triisopropylsilanyloxy-phenyl)-(2-ethyl-pyridin-3-yl)-amine as described for Example 80. (3-Bromo-5-triisopropylsilanyloxy-phenyl)-(2-ethyl-pyridin-3-yl)-amine was converted to 3-(2-ethyl-pyridin-3-ylamino)-5-(1H-indol-4-yl)-phenol as described in Example 35. 1H NMR (400 MHz, CD3OD): δ 8.02 (d, J=4.8 Hz 1H), 7.66 (dd, J=8.0, 1.5 Hz, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.22 (d, J=3.1 Hz, 1H), 7.14-7.10 (m, 2H), 7.03 (d, J=7.0 Hz, 1H), 6.76 (t, J=1.6 Hz, 1H), 6.69 (s, 1H), 6.61 (d, J=3.3 Hz, 1H), 6.40 (t, J=2.1 Hz, 1H), 2.86 (q, J=7.5 Hz, 2H), 1.25 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record
ord-2f74dff4fa8a4476b2ec7430d068868b
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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