1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indol-4-ol → 1-ethyl-6-fluoro-3-(piperidin-3-yl)-1H-indol-4-ol

HRID 1404149Notes

Reaction equation

HRID 1404149 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([F:12])[CH:8]=[C:7]([OH:13])[C:6]=2[C:5]([CH2:14][CH2:15][N:16]2[CH2:24][C:23]3[C:18](=CC=CC=3)C2)=[CH:4]1)[CH3:2].C(N1CCCC(C2C3C(=CC(F)=CC=3OCC3C=CC=CC=3)N(CC)C=2)=C1)C1C=CC=CC=1>>[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([F:12])[CH:8]=[C:7]([OH:13])[C:6]=2[C:5]([CH:14]2[CH2:18][CH2:23][CH2:24][NH:16][CH2:15]2)=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 509963501-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indol-4-olHCID 583039133-(1-benzyl-1,4,5,6-tetrahydropyridin-3-yl)-4-(benzyloxy)-1-ethyl-6-fluoro-1H-indole

Product 1

HCID 509963461-ethyl-6-fluoro-3-(piperidin-3-yl)-1H-indol-4-olYield 59%

Procedure

Following the procedure (step 3 scheme 31 used to prepare compound 31-4 compound 38-3 gave compound 38-4 (113 mg, 59%) as a light tan-colored solid. 1H NMR (300 MHz, MeOD-d6): δ (ppm) 6.80 (s, 1H), 6.49 (dd, J=10.0, 2.1 Hz, 1H), 6.13 (dd, J=11.4, 2.1 Hz, 1H), 4.01 (q, J=7.2 Hz, 2H), 3.53-3.40 (m, 2H), 3.05 (d, J=11.4 Hz, 1H), 2.55 (dt, J=23.0, 11.7 Hz, 2H), 2.14 (dd, J=8.8, 6.1 Hz, 1H), 1.85-1.56 (m, 3H), 1.34 (t, J=7.2 Hz, 3H). LCMS: calc 262.1 and found: 263.1 [MH]+.

Sources & evidence

ORD record
ord-314ebef29def4b4e960a2dadb73cb67b
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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