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Water → 1h-Indazole-1-carboxylic acid,3-[(4-ethylphenyl)methyl]-,1,1-dimethylethyl ester

HRID 1625861
Notes
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Reaction equation

HRID 1625861 reaction equation
O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[C:17]([O:21][C:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](I)=[N:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].[Br-].[CH2:35]([C:37]1[CH:44]=[CH:43][C:40]([CH2:41][Zn+])=[CH:39][CH:38]=1)[CH3:36].O>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:17]([O:21][C:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:41][C:40]2[CH:43]=[CH:44][C:37]([CH2:35][CH3:36])=[CH:38][CH:39]=2)=[N:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 521585Tris(furan-2-yl)phosphaneHCID 11473390tert-butyl 3-iodo-1H-indazole-1-carboxylateHCID 178436323HCID 178436323, compound

Product 1

HCID 666081711h-Indazole-1-carboxylic acid,3-[(4-ethylphenyl)methyl]-,1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tris(dibenzylideneacetone)dipalladium (0) (167 mg) and tri(2-furyl)phosphine (135 mg) in tetrahydrofuran (20 ml) was stirred at room temperature for 5 minutes under argon atmosphere. Thereto were added 1-t-butoxycarbonyl-3-iodo-1H-indazole (2.0 g) and the above 4-ethylbenzylzinc bromide (N,N-dimethylformamide solution) at 0° C., and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The extract was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-92:8) to give 1-t-butoxycarbonyl-3-(4-ethylphenylmethyl)-1H-indazole (1.37 g) as colorless oil. APCI-Mass m/Z 337 (M+H).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-92:8)

Sources & evidence

ORD record
ord-85d24b43aba44a44bcf5dace3a2bde71
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785403B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes