Hydrochloric Acid → HCID 22479836, compound

HRID 1349641Notes

Reaction equation

HRID 1349641 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](/[CH:17]=[CH:18]/[C:19]([O:21]CC)=[O:20])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22479831HCID 22479831, compound

Product 1

HCID 22479836HCID 22479836, compoundYield 476.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2E)-3-[3-(4-fluorophenyl)-1H-indazol-5-yl]prop-2-enoate (0.10 g, 0.32 mmol) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide (0.032 mg, 1.6 mmol) in water (5 mL) and the mixture was stirred at ambient temperature overnight. The reaction mixture was acidified with 6 N hydrochloric acid solution to give a white solid. It was then purified by HPLC to provide the title compound (0.43 g, 48% yield): 1H NMR (DMSO-d6) δ 13.45 (br s, 1H), 12.28 (br s, 1H), 8.39 (s, 1H), 8.11 (d, 1H), 8.10 (d, 1H), 7.83 (d, 1H), 7.79 (d, 1H), 7.60 (d, 1H), 7.35 (t, 2H), 6.57 (d, 1H); ES-MS (m/z) 283 [M+1]+.

Workup

  1. customto give a white solid
  2. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-707e9469971f47e1851aba1ab2bfbc3b
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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