2-(Benzyloxy) ethanol → 2-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)ethanol

HRID 1882263Notes

Reaction equation

HRID 1882263 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]3[C:13]=2[C:14]2[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[CH2:27]([O:34]CCO)[C:28]1C=CC=CC=1>[Pd].[H][H]>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([O:21][CH2:28][CH2:27][OH:34])=[C:17]3[C:13]=2[C:14]2[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 121412-(Benzyloxy) ethanolHCID 588800815-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-ol

Product 1

HCID 588801692-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)ethanol

Reagents, catalysts & solvents 1

HCID 178506449HCID 178506449, compoundCatalyst

Procedure

The title compound was synthesized from Compound 157 and 2-(benzyloxy)ethanol using an analogous procedure to that outlined in the preparation of Compound 210 followed by debenzylation using Pd/C—H2. 1H NMR (400 MHz, Methanol-d4) δ 8.30 (s, 1H) 8.19 (m, 1H) 8.06 (m, 1H) 8.00 (m, 2H) 7.87 (t, J=8.0 Hz, 1H) 7.26 (m, 2H) 4.38 (t, J=4 Hz, 2H) 4.08 (t, J=4 Hz, 2H) 3.30 (q, J=7.5 Hz, 2H) 2.41 (s, 3H) 1.31 (t, J=7.5 Hz, 3H). [M+H] calc'd for C22H23N2O4S, 411; found, 411.

Sources & evidence

ORD record
ord-a9125439453849aaaba7e6b6b4728420
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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