Ethyl bromoacetate → Ethyl [5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]acetate

HRID 2189776Notes

Reaction equation

HRID 2189776 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:26])[CH3:25])=[C:19]([CH:22]=4)[C:20]#[N:21])[O:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>>[C:20]([C:19]1[CH:22]=[C:15]([C:13]2[O:12][N:11]=[C:10]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[N:1]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:2]=[CH:3]4)[N:14]=2)[CH:16]=[CH:17][C:18]=1[O:23][CH:24]([CH3:26])[CH3:25])#[N:21]

Participants

3

Reactant 2

HCID 7748Ethyl bromoacetateHCID 532473675-[3-(1H-indazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

Product 1

HCID 59316757Ethyl [5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]acetate

Procedure

Prepared in a similar fashion to (D44) from 5-[3-(1H-indazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile (D43) and ethyl bromoacetate. The crude material was purified by trituration with diethyl ether to give the title compound as a yellow solid. MS (ES) C23H21N5O4 requires 431; found (MH+) 432.

Workup

  1. customThe crude material was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-26b56bef472040d095df1b77b9ec8d73
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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