Triethyl Phosphate → HCID 58415248, compound

HRID 2075173Notes

Reaction equation

HRID 2075173 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([CH:21]=1)/[CH:7]=[N:8]/[C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[F:20].P(OCC)(OCC)(OCC)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[CH:7][N:8]([C:9]3[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=3[F:20])[N:22]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 6535Triethyl PhosphateHCID 178469011HCID 178469011, compound

Product 1

HCID 58415248HCID 58415248, compound

Procedure

A mixture of (E)-ethyl 4-(5-bromo-2-nitrobenzylideneamino)-3-fluorobenzoate (432 mg, 1.09 mmol) and triethyl phosphate (1.5 mL, 9.0 mmol) was irradiated in a microwave instrument at 150° C. for 1.5 h. The cooled reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate) to give ethyl 4-(5-bromo-2H-indazol-2-yl)-3-fluorobenzoate as pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.56 (d, J=2.0 Hz, 1H), 8.25 (t, J=7.8 Hz, 1H), 8.02-7.90 (m, 2H), 7.89 (d, J=0.8 Hz, 1H), 7.66 (d, J=9.2 Hz, 1H), 7.40 (dd, J=1.6, 9.2 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 1.44 (t, J=7.2 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −123.4. MS (ESI) m/z: Calculated: 363.18; Observed: 363.2 (M++1).

Workup

  1. customwas irradiated in a microwave instrument at 150° C. for 1.5 h
  2. customThe cooled reaction mixture
  3. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bc1fcd6161be4843aa5214230caf4f83
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

Loading…