Cesium carbonate → HCID 67981389, compound

HRID 1520088Notes

Reaction equation

HRID 1520088 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[C:10]([C:18]3[N:19]=[N:20][N:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[O:30])=[CH:25][CH:24]=4)[CH:22]=3)=[N:9]2)=[CH:5][CH:4]=1.Br[CH2:40][CH2:41][CH2:42][OH:43].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:40][CH2:41][CH2:42][OH:43])=[CH:14][CH:15]=3)[C:10]([C:18]3[N:19]=[N:20][N:21]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([N:31]5[CH2:32][CH2:33][O:34][CH2:35][CH2:36]5)=[O:30])=[CH:27][CH:28]=4)[CH:22]=3)=[N:9]2)=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 67981050HCID 67981050, compound

Product 1

HCID 67981389HCID 67981389, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-methoxybenzyl)-3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-5-ol (60 mg; 0.12 mmol; 1.0 eq.), 3-bromo-1-propanol (24 mg; 0.18 mmol; 1.5 eq.) and cesium carbonate (77 mg; 0.24 mmol; 2.0 eq.) in DMF (1.2 mL) was stirred at RT O/N. The reaction mixture was then diluted with DCM and washed with brine. Organic phase was dried over magnesium sulfate, filtered and concentrated. Purification of the crude by preparative HPLC gave the title compound as a white powder (43 mg, 64%).

Workup

  1. washwashed with brine
  2. dry with materialOrganic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude by preparative HPLC

Sources & evidence

ORD record
ord-8341a7b2a2f4426ab0220849cce213b2
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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