Butyl bromide → HCID 178450299, compound

HRID 1027523Notes

Reaction equation

HRID 1027523 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[N:13][NH:14][CH:15]=2)C=CC=CC=1.BrCCCC.N1C=CC=C(C2C(O)=CN(COCC[Si](C)(C)C)N=2)C=1>CCOCC.C(OCC)(=O)C>[CH2:9]([O:10][C:11]1[C:12]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:13][NH:14][CH:15]=1)[CH2:8][CH2:7][CH3:1]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 57548087HCID 57548087, compoundHCID 178420268HCID 178420268, compound

Product 1

HCID 178450299HCID 178450299, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

Compound 32C was prepared following the procedure as described for the synthesis of compound 32A (see Scheme 5) using 1-bromo-butane as the alkyl halogenide and 3-pyridin-3-yl-1-(2-trimethylsilanyl-1-ethoxymethyl)-1H-pyrazol-4-ol (30). Work-up and flash chromatography (ethyl acetate/diethyl ether 1/1) afforded compound 31C. Yield 30% (oil). 1H-NMR (major isomer is given, 400 MHz, CDCl3): δ 8.9 (d, J=2 Hz, 1H), 8.6 (dd, J=5 Hz, 2 Hz, 1H), 8.05 (dt, J=8 Hz, 2 Hz, 1H), 7.42 (s, 1H), 7.41-7.37 (m, 1H), 5.37 (s, 2H), 3.98 (t, J=7 Hz, 2H), 3.74-3.68 (m, 2H), 1.74-1.66 (m, 2H), 1.49-1.39 (m, 2H), 0.92 (t, J=7 Hz, 3H), 0.02 (s, 9H).

Sources & evidence

ORD record
ord-4fba2dfaecd64ceca9cd580ae8991831
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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