Water → HCID 178480245, compound

HRID 2107402Notes

Reaction equation

HRID 2107402 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH:17]3[CH2:22][CH2:21][N:20]([C:23](OC)=O)[CH2:19][CH2:18]3)=[N:13][NH:14]2)=[CH:10][CH:9]=1.O>O1CCCC1>[F:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[N:13][NH:14]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178501917HCID 178501917, compound

Product 1

HCID 178480245HCID 178480245, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension, under nitrogen, of 4.7 g of lithium aluminum hydride (50-55% oil dispersion) in 90 ml of tetrahydrofuran was added, dropwise, 8.9 g of 6-fluoro-3-(1-methoxycarbonyl-4-piperidinyl)-1H-indazole, dissolved in 50 ml of tetrahydrofuran. After the addition was complete, the reaction was heated under reflux for 2 hr. The reaction was cooled in an ice-salt bath and water was carefully added. The mixture was filtered and the filter cake was washed with tetrahydrofuran and twice with hot methanol. The filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate to yield 5.1 g (68%) of product, mp 217°-220°. Recrystallization from ethanol (twice) provided the analytical sample, mp 218°-220° C.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was heated
  3. temperatureunder reflux for 2 hr
  4. temperatureThe reaction was cooled in an ice-salt bath
  5. filtrationThe mixture was filtered
  6. washthe filter cake was washed with tetrahydrofuran and twice with hot methanol
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-9eb51cd26c6a460189332db14859f7ba
Source dataset
uspto-grants-1990_06
Patent number
US04933460

Reaction notes

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