4-Chlorobenzaldehyde → 2-[(4-cyano-3-fluoro-phenyl)-hydroxy-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

HRID 2204406Notes

Reaction equation

HRID 2204406 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[C:11]([O:18][CH3:19])=[N:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=2)[N:7]([CH:20]([CH3:22])[CH3:21])[CH:6]=1)=[O:4].[F:23][C:24]1[CH:31]=[C:30]([CH:32]=[O:33])[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].COC(C1C=C(Br)N(C(C)C)C=1)=O.ClC1C=CC(C=O)=CC=1>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[C:11]([O:18][CH3:19])=[N:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=2)[N:7]([CH:20]([CH3:22])[CH3:21])[C:6]=1[CH:32]([C:30]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([F:23])[CH:31]=1)[OH:33])=[O:4]

Participants

5

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 112173392-Fluoro-4-formylbenzonitrileHCID 86703102Methyl 5-bromo-1-isopropyl-1H-pyrrole-3-carboxylateHCID 867032195-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867032182-[(4-cyano-3-fluoro-phenyl)-hydroxy-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Procedure

The title compound was prepared in analogy to the procedure described for Step D3 but 5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step 195.3) and 2-fluoro-4-formyl-benzonitrile [101048-76-4] were used instead of 5-bromo-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester and 4-chlorobenzaldehyde respectively. The title compound was obtained as a yellow solid. tR: 1.12 min (HPLC 3); ESI-MS: tR=1.11 min, [M+H]+ 455 (LC-MS 1); TLC: Rf=0.30 (1:1 EtOAc/heptanes).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-d539b57856cf402ebd4e65856c6ccb27
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…