Cesium carbonate → HCID 15956107, compound

HRID 1473998Notes

Reaction equation

HRID 1473998 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1>CC(C)=O>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:9][C:2]=1[O:1][CH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1)#[N:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 151114782-(Bromomethyl)thiazoleHCID 860960092-Hydroxy-4-(thiazol-2-ylamino)benzonitrile

Product 1

HCID 15956107HCID 15956107, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method B, a mixture of 2-hydroxy-4-(thiazol-2-ylamino)benzonitrile (70 mg, 0.32 mmol) and Cs2CO3 (105 mg, 0.32 mmol) in acetone (4.4 mL) was treated with 2-bromomethylthiazole (57 mg, 0.32 mmol) at RT. Reaction control by TLC showed full conversion after 4 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 4/6) in 8 yield (8 mg).

Workup

  1. customReaction control by TLC
  2. customafter 4 h

Sources & evidence

ORD record
ord-d842075ab1714fca82956b2360e8c792
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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