Benzo(B)Thiophene-2-Boronic Acid → Methyl 3-Benzo[B]Thiophen-2-Yl-1H-Indazole-5-Carboxylate

HRID 1353717Notes

Reaction equation

HRID 1353717 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=C(C(N)=O)[CH:9]=2)[N:4](C2CCCCO2)[N:3]=1.[S:20]1[C:24](B(O)O)=[CH:23][C:22]2[CH:28]=[CH:29][CH:30]=[CH:31][C:21]1=2.ClCCl.P([O-])([O-])([O-])=[O:36].[K+].[K+].[K+].[CH3:43][O:44][CH2:45][CH2:46]OC>>[S:20]1[C:24]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:46]([C:45]([O:44][CH3:43])=[O:36])[CH:9]=3)[NH:4][N:3]=2)=[CH:23][C:22]2[CH:28]=[CH:29][CH:30]=[CH:31][C:21]1=2

Participants

6

Reactant 5

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 224799153-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

Product 1

HCID 22480065Methyl 3-Benzo[B]Thiophen-2-Yl-1H-Indazole-5-CarboxylateYield 26%

Procedure

A mixture of 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide (425 mg, 1.31 mmol), benzo[b]thiophene-2-boronic acid (348 mg, 1.95 mmol, 1.49 equiv.), [1,1′-bis(diphenylphosphino)-ferrocene} dichloropalladium (II) complex with dichloromethane (107 mg, 0.131 mmol, 0.10 equiv.), potassium phosphate (K3PO4, 1.38 g, 6.50 mmol, 4.96 equiv.) and 6.5 mL of DME were refluxed for 18 h and concentrated. Purification by silica gel chromatography using 0–5% MeOH in EtOAc as eluent afforded the title compound (126 mg, 26% yield): ES-MS (m/z) 378 [M+1]+.

Workup

  1. temperaturewere refluxed for 18 h
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-d60a49cb8d3641499dac0eaf5cd1ec30
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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