1-(4-(bromomethyl)phenyl)-1H-1,2,4-triazole → 2-Tert-butoxy-2-[4-chroman-6-yl-6-methyl-1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]pyrrolo[2,3-b]pyridin-5-yl]acetic acid

HRID 1912583Notes

Reaction equation

HRID 1912583 reaction equation
[C:1]([O:5][CH:6]([C:11]1[C:12]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[O:27][CH2:26][CH2:25][CH2:24]3)=[C:13]2[CH:20]=[CH:19][NH:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH:43]=[N:42][CH:41]=[N:40]2)=[CH:35][CH:34]=1>>[N:39]1([C:36]2[CH:37]=[CH:38][C:33]([CH2:32][N:18]3[C:14]4=[N:15][C:16]([CH3:17])=[C:11]([CH:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:7]([OH:9])=[O:8])[C:12]([C:21]5[CH:22]=[C:23]6[C:28](=[CH:29][CH:30]=5)[O:27][CH2:26][CH2:25][CH2:24]6)=[C:13]4[CH:20]=[CH:19]3)=[CH:34][CH:35]=2)[CH:43]=[N:42][CH:41]=[N:40]1

Participants

3

Reactant 2

HCID 27764891-(4-(bromomethyl)phenyl)-1H-1,2,4-triazoleHCID 71209024methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 712092152-Tert-butoxy-2-[4-chroman-6-yl-6-methyl-1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]pyrrolo[2,3-b]pyridin-5-yl]acetic acid

Procedure

The title compound was prepared in a manner similar to that described in Example 27, Step H from methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate and 1-(4-(bromomethyl)phenyl)-1H-1,2,4-triazole. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.61 (br. s., 1 H), 8.13 (br. s., 1 H), 7.67 (d, J=8.4 Hz, 2 H), 7.52-7.39 (m, 3 H), 7.24-7.17 (m, 1 H), 7.12 (t, J=3.1 Hz, 1 H), 6.95 (dd, J=4.7, 8.4 Hz, 1 H), 6.37 (dd, J=3.5, 11.3 Hz, 1 H), 5.80-5.70 (m, 1 H), 5.64-5.52 (m, 2 H), 4.30 (t, J=4.2 Hz, 2 H), 2.96-2.77 (m, 5 H), 2.16-2.05 (m, 2 H), 1.05-0.91 (s, 9 H); LC/MS (m/z) ES+=552.39 (M+1).

Sources & evidence

ORD record
ord-4c59a235e6ae406b8ba64128219316c3
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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