Water → HCID 59477635, compound

HRID 1516586Notes

Reaction equation

HRID 1516586 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16]([C:20]#[N:21])=[CH:17][NH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([O:24][C:25](=[O:37])[C:26]1[CH:31]=[CH:30][C:29](F)=[CH:28][C:27]=1[O:33][CH2:34][O:35][CH3:36])[CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:22]([O:24][C:25](=[O:37])[C:26]1[CH:31]=[CH:30][C:29]([N:18]2[CH:19]=[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]([C:20]#[N:21])=[CH:17]2)=[CH:28][C:27]=1[O:33][CH2:34][O:35][CH3:36])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 59224848HCID 59224848, compoundHCID 594780304-[2-(Benzyloxy)phenyl]-1H-pyrrole-3-carbonitrile

Product 1

HCID 59477635HCID 59477635, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-(2-benzyloxyphenyl)-1H-pyrrole-3-carbonitrile (1.5 g), 4-fluoro-2-methoxymethoxybenzoic acid ethyl ester (1.4 g) in N,N-dimethylformamide (25 mL) was added cesium carbonate, and this mixture was stirred at 65° C. for 15 hours. This reaction mixture was poured into water, the precipitated solid was collected by filtration, and washed with water and n-hexane, dried under reduced pressure at 50° C. to give the title compound (2.3 g).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water and n-hexane
  3. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-0dcd798553e44c16a27fddd3792f0bb1
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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