Aluminium lithium hydride → N-(3-(4-Fluorobenzyl)-3-(hydroxymethyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

HRID 530877Notes

Reaction equation

HRID 530877 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][C:7]2([C:32](OC)=[O:33])[CH2:12][CH2:11][CH2:10][CH:9]([NH:13][C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[C:19]4[C:25]3[CH:30]=[CH:29][N:28]=[C:27]([CH3:31])[CH:26]=3)=[O:15])[CH2:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][C:7]2([CH2:32][OH:33])[CH2:12][CH2:11][CH2:10][CH:9]([NH:13][C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[C:19]4[C:25]3[CH:30]=[CH:29][N:28]=[C:27]([CH3:31])[CH:26]=3)=[O:15])[CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67985855methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)cyclohexanecarboxylate

Product 1

HCID 68074191N-(3-(4-Fluorobenzyl)-3-(hydroxymethyl)cyclohexyl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a flask, methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)cyclohexanecarboxylate (0.31 mmol) was dissolved in tetrahydrofuran (6 mL). Lithium aluminum hydride in THF (1M) (0.62 ml, 0.62 mmol) was added to the flask. The reaction was stirred for 3 hrs at room temperature. Upon completion, the reaction was quenched with ethyl acetate (5 ml) drop-wise. Water (5 mL) was added to the reaction. The reaction mixture then was extracted 3 times with ethyl acetate (20 mL). The organic layers were combined, were dried with sodium sulfate, concentrated and purified using HPLC to give the titled compound. LC-MS: 473.23 [M+H]. LC/MS RT=2.46 min.

Workup

  1. customUpon completion, the reaction was quenched with ethyl acetate (5 ml) drop-wise
  2. additionWater (5 mL) was added to the reaction
  3. extractionThe reaction mixture then was extracted 3 times with ethyl acetate (20 mL)
  4. dry with materialwere dried with sodium sulfate
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-f27335346bdf4d02a2a0d2c49665d07a
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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