Lithium hydroxide, monohydrate → HCID 59024107, compound

HRID 1678241Notes

Reaction equation

HRID 1678241 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[CH:18]=3)[CH:16]=1)[NH:13][N:12]=[CH:11]2)=[O:7]>O1CCOCC1.O>[S:21]1[C:17]([C:15]2[CH:16]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]1=2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59023812HCID 59023812, compound

Product 1

HCID 59024107HCID 59024107, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

Lithium hydroxide monohydrate (2.25 g, 53.5 mmol) was added to a suspension of methyl-7-benzo[b]thiophen-2-yl-1H-indazole-5-methanoate (3.37 g, 10.71 mmol) in a mixture of 1,4-dioxane (65 mL) and water (9 mL). The mixture was heated to about 65° C. for about 18 hours then cooled to about 40° C. and filtered. The filtrate was acidified with aqueous hydrochloric acid (1N, 54 mL) and the resulting precipitate was collected by filtration and dried under reduced pressure to give 7-benzo[b]thiophen-2-yl-1H-indazole-5-carboxylic acid (3.16 g, 100%); 1H NMR (DMSO-d6, 400 MHz) δ 13.56 (bs, 1H), 8.51 (d, 1H), 8.47 (s, 1H), 8.14 (d, 1H), 8.04 (d, 1H), 7.94 (d, 1H), 7.45 (d, 2H); RP-HPLC (Table 1, Method e) Rt=1.06, m/z: (M−H)− 292.8.

Workup

  1. temperaturethen cooled to about 40° C.
  2. filtrationfiltered
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-5ce4238760c44cae9e81ece48bb33b66
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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