Ethyl bromoacetate → HCID 1214949, compound

HRID 910017Notes

Reaction equation

HRID 910017 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:11]=[N:12][N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1)=[O:9].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[C:15]1([N:13]2[CH:14]=[C:10]([C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:1][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:9])[CH:11]=[N:12]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 7748Ethyl bromoacetateHCID 688697(2-Hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone

Product 1

HCID 1214949HCID 1214949, compoundYield 67%

Procedure

Prepared from (2-hydroxyphenyl)-(1-phenyl-1H-pyrazol-4-yl)ketone (264 mg, 1.0 mmol) and ethyl bromoacetate according to GP2 to give 235 mg (67%) of the title compound as white solid: 1H NMR (CDCl3): δ 1.26 (t, J=7.1 Hz, 3H), 4.24 (q, J=7.1 Hz, 2H), 4.67 (s, 2H), 6.84 (d, J=8.3 Hz, 1H), 7.10 (ts, J=7.4, 0.8 Hz, 1 Hz), 7.29-7.36 (m, 1H), 7.41-7.53 (m, 4H), 7.72-7.78 (m, 2H), 8.18 (s, 1H), 8.58 (s, 1H); 13C NMR (CDCl3): δ 14.3, 61.7, 65.4, 112.2, 118.8, 119.3, 119.7, 120.0, 122.1, 125.8, 127.6, 129.7, 129.9, 130.1, 130.6, 131.8, 132.1, 136.3, 139.7, 142.8, 155.0, 168.9, 188.7.

Sources & evidence

ORD record
ord-be15db0ce0304dabb99826cd22d36bb0
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

Loading…