Methyl iodide → 3-(1-methyl-1H-indol-4-yl)-5-(pyridin-3-ylamino)-phenol

HRID 1784817Notes

Reaction equation

HRID 1784817 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)[O:3]1.[CH3:19]I.Br[C:22]1[CH:23]=[C:24]([NH:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)[CH:25]=[C:26]([O:28]CC2C=CC(OC)=CC=2)[CH:27]=1>>[CH3:22][N:13]1[C:14]2[C:10](=[C:9]([B:4]3[O:3][C:2]([CH3:18])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1.[CH3:19][N:13]1[C:14]2[C:10](=[C:9]([C:22]3[CH:27]=[C:26]([OH:28])[CH:25]=[C:24]([NH:38][C:39]4[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=4)[CH:23]=3)[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 50994028[3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine

Product 2

HCID 156044233-(1-methyl-1H-indol-4-yl)-5-(pyridin-3-ylamino)-phenolHCID 185257851-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Procedure

1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole was prepared from 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole and methyl iodide, and was coupled with [3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine in the same manner as described for Example 25. Deprotection was carried out as described for Example 34 to give 3-(1-methyl-1H-indol-4-yl)-5-(pyridin-3-ylamino)-phenol. 1H NMR (400 MHz, CD3OD): δ 8.32 (br s, 1H), 7.98 (br s, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.42-7.36 (m, 1H), 7.34 (d, J=8.2 Hz, 1H), 7.21 (d, J=7.2 Hz, 1H), 7.19-7.17 (m, 1H), 7.08 (dd, J=7.2, 0.8 Hz, 1H), 6.91 (t, J=1.7 Hz, 1H), 6.79-6.77 (m, 1H), 6.62 (t, J=2.0 Hz, 1H), 6.59 (d, J=3.1 Hz, 1H), 3.81 (s, 3H).

Sources & evidence

ORD record
ord-d77c24d3aeee4112bb43e55d41702be6
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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