3-Benzyloxy-1-propanol → 3-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)propan-1-ol

HRID 1642572Notes

Reaction equation

HRID 1642572 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]CCCO)[C:28]1C=CC=C[CH:29]=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][CH2:29][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 3479713-Benzyloxy-1-propanolHCID 588800815-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-ol

Product 1

HCID 588801363-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 178506449HCID 178506449, compoundCatalyst

Procedure

The title compound was synthesized from Compound 157 and 3-(benzyloxy)propan-1-ol using an analogous procedure to that outlined in the preparation of Compound 210 followed by debenzylation using Pd/C—H2 .1H NMR (400 MHz, DMSO-d6) δ ppm 1.18 (t, J=7.33 Hz, 3 H) 2.01 (t, J=6.19 Hz, 2 H) 2.27 (s, 3 H) 3.41 (q, J=7.33 Hz, 2 H) 3.72 (q, J=5.98 Hz, 2 H) 4.30 (t, J=6.19 Hz, 2 H) 4.57 (t, J=5.18 Hz, 1 H) 7.06-7.17 (m, 2 H) 7.55 (s, 1 H) 7.85 (t, J=7.71 Hz, 1 H) 8.00 (br. s., 1 H) 7.98 (d, J=5.05 Hz, 2 H) 8.08 (s, 1 H) 8.28 (s, 1 H) 11.99 (s, 1 H); ESI-MS: m/z calc'd for C23H24N2O4S 424.15; found 425.3 (M+H)+

Sources & evidence

ORD record
ord-aff3771c69b6485ebe21d654f9f7419a
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

Loading…