Potassium Phosphate, Tribasic → HCID 57636437, compound

HRID 2110265Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[C:10](I)=[N:9]1)=O)(C)(C)C.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:10]1[C:11]2[C:16](=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[NH:8][N:9]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-Iodo-6-nitro-indazole-1-carboxylic acid tert-butyl ester (5.83 g, 14.98 mmol) in 200 mL toluene was added 2-chlorophenyl boronic acid (4.48 g, 28.46 mmol), K3PO4 (7.82 g), Pd2(dba)3 (41.53 mg) and 2-(dicyclohexylphosphino)-2′-methylbiphenyl) (436.68 mg). The reaction mixture was heated to 110° C. and stirred at this temperature for 36 hours. The reaction mixture was cooled and partitioned between water and EtOAc. The orgaic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to give 8.82 g of crude 3-(2-Chloro-phenyl)-6-nitro-1H-indazole, MS (M+H)=275.

Workup

temperatureThe reaction mixture was cooled
custompartitioned between water and EtOAc
customThe orgaic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3869224e5fc24f56848a4bfd462a6b39
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517901B2

Reaction notes

Loading…