HCID 15859007, compound → HCID 22481037, compound

HRID 412681Notes

Reaction equation

HRID 412681 reaction equation
[CH:1]1([C:6]2[C:15]([C:16](=[O:27])[C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)[C:13]3[C:12](=[O:36])[CH2:11][C:10]([CH3:38])([CH3:37])[CH2:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCCC1>[CH:1]1([C:6]2[C:15]([C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][CH:18]=3)=[O:27])=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)[C:13]3[CH:12]([OH:36])[CH2:11][C:10]([CH3:38])([CH3:37])[CH2:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 15859007HCID 15859007, compound

Product 1

HCID 22481037HCID 22481037, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.1 g (4 mmol) of 2-cyclopentyl-4-(3,4-difluorophenyl)-7,7-dimethyl-3-(4 trifluoromethylbenzoyl)-7,8-dihydro-6H-quinolin-5-one were dissolved in 20 ml of tetrahydrofuran and, at 0° C., added dropwise to a solution of 0.2 g (1.2 mmol) of 1R,2S-aminoindanol and 2.7 ml (16 mmol) of boranediethylaniline complex in 2 ml of THF. The mixture is stirred at RT overnight. After about 20 hours, the reaction was quenched using 2.4 ml of 1,2-ethanediol. The tetrahydrofuran was distilled off, the resulting oil was taken up in ethyl acetate and the organic phase was, after washing with 2N hydrochloric acid and saturated sodium bicarbonate solution, dried and concentrated. The residue was recrystallized from hot cyclohexane. This gave a total of 1.4 g of colourless crystals of melting point: 166-168° C.

Workup

  1. waitAfter about 20 hours
  2. customthe reaction was quenched
  3. distillationThe tetrahydrofuran was distilled off
  4. washafter washing with 2N hydrochloric acid and saturated sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from hot cyclohexane

Sources & evidence

ORD record
ord-95f26c40ff33443f8815672cc611489d
Source dataset
uspto-grants-2003_05
Patent number
US06562976B2

Reaction notes

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