Ethyl bromoacetate → HCID 44724849, compound

HRID 910018Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([C:11]2[CH:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:15]=2)=[O:10])[CH:3]=1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:4]([C:9]([C:11]2[CH:12]=[N:13][N:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:15]=2)=[O:10])[CH:3]=1

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 854139(5-Fluoro-2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone

Product 1

HCID 44724849HCID 44724849, compoundYield 91%

Procedure

Prepared from 4-fluoro-2-(1-phenyl-1H-pyrazole-4-carbonyl)phenol (282 mg) and ethyl bromoacetate according to GP2 to give 335 mg (91%) yellow solid: LC/MS (an10n8): Rt 3.16, m/z 339.0 [M−H]−; 1H NMR (CDCl3): δ 1.26 (t, J=7.0 Hz, 3H), 4.23 (t, J=7.1 Hz, 2H), 4.63 (s, 2H), 6.81 (dd, J=9.0, 4.0 Hz, 1H), 7.13 (ddd, J=8.9, 4.5, 3.0 Hz, 1H), 7.21 (dd, J=8.1, 3.2 Hz, 1H), 7.31-7.37 (m, 1H), 7.24-7.50 (m, 2H), 7.72-7.78 (m, 2H), 8.18 (s, 1H), 8.58 (s, 1H); 13C NMR (CDCl3): δ14.3, 61.8, 66.1, 114.0 (d, JCF=7.6 Hz), 116.8 (d, JCF=24.5 Hz), 118.3 (d, JCF=23.5 Hz), 119.7, 125.2, 127.7, 129.7, 131.8, 139.6, 142.8, 151.1 (d, JCF=2.2 Hz), 157.6 (d, JCF=241.1 Hz), 168.7, 187.1.

Sources & evidence

ORD record: ord-31d1525d6c0244a08954c015113094b9
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022063B2

Reaction notes

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