Hydrochloric Acid → Methyl 3-Benzo[B]Thiophen-2-Yl-1H-Indazole-5-Carboxylate

HRID 1349652Notes

Reaction equation

HRID 1349652 reaction equation
[S:1]1[C:5]([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15](N)=[O:16])[CH:13]=3)[N:8](C3CCCCO3)[N:7]=2)=[CH:4][C:3]2[CH:24]=[CH:25][CH:26]=[CH:27][C:2]1=2.Cl.[OH-:29].[Na+].[CH3:31]O>>[S:1]1[C:5]([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:29][CH3:31])=[O:16])[CH:13]=3)[NH:8][N:7]=2)=[CH:4][C:3]2[CH:24]=[CH:25][CH:26]=[CH:27][C:2]1=2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 224799633-benzo[b]thiophen-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide

Product 1

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

Conditions

Temperature
65 °C

Procedure

A mixture of 3-benzo[b]thiophen-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide (126 mg, 0.334 mmol), 10.0 mL of MeOH, and 10.0 mL of 6.0 N aq. HCl were heated at 65° C. for 24 h. The reaction mixture was added dropwise to 50 mL of 6.0 N aq. NaOH with stirring. This mixture was extracted with 3×EtOAc and the combined organics were dried (Na2SO4). Purification by silica gel chromatography using 30–40% EtOAc in hexanes afforded the title compound (27.0 mg, 26% yield): 1H NMR (DMSO-d6) δ 13.75 (br s, 1H), 8.84 (s, 1H), 8.19 (s, 1H), 8.15–7.95 (m, 3H), 7.74 (d, 1H), 7.45–7.35 (m, 2H), 3.94 (s, 3H); ES-MS (m/z) 378 [M+1]+.

Workup

  1. extractionThis mixture was extracted with 3×EtOAc
  2. dry with materialthe combined organics were dried (Na2SO4)
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-d1a5227900a94a608adb26ab72ce01a2
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…