Methanol → HCID 59023812, compound

HRID 1678240Notes

Reaction equation

HRID 1678240 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8](Br)[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.C(N(CC)CC)C.[CH3:27][OH:28].CN(C)[CH:31]=[O:32]>>[CH3:27][O:28][C:31]([C:8]1[CH:9]=[C:10]2[C:14](=[C:6]([C:5]3[S:1][C:2]4[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=4[CH:4]=3)[CH:7]=1)[NH:13][N:12]=[CH:11]2)=[O:32]

Participants

5

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 59024282HCID 59024282, compound

Product 1

HCID 59023812HCID 59023812, compoundYield 80%

Conditions

Temperature
90 °C

Procedure

A solution of 7-benzo[b]thiophen-2-yl-5-bromo-1H-indazole (Preparation #26, 4.5 g, 13.7 mmol) in N,N-dimethylformamide (100 mL) was degassed and purged with carbon monoxide. Triethylamine (4.1 g, 41 mmol), methanol (13.1 g, 410 mmol) and dichloro[bis(triphenylphosphine)]palladium (II) (1.45 g, 2.05 mmol) were added and the mixture was heated to about 90° C. for about 15 hours. The mixture was cooled and the solvent was removed under reduced pressure. The residue was triturated with ethyl acetate (75 mL) and water (35 mL) then further purified by flash chromatography over silica gel using dichloromethane/ethyl acetate (95:5) as the eluent to give methyl-7-benzo[b]thiophen-2-yl-1H-indazole-5-methanoate (3.37 g, 80%).

Workup

  1. custompurged with carbon monoxide
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was triturated with ethyl acetate (75 mL) and water (35 mL)
  5. customthen further purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-06dd244903fd49a993827525a31c373f
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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