Aluminium lithium hydride → HCID 59631308, compound

HRID 1431656Notes

Reaction equation

HRID 1431656 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:33]=1)=[C:5]([CH3:26])[C:6]([C:13]1[CH:14]=[C:15]([C:23](=[O:25])[CH3:24])[CH:16]=[CH:17][C:18]=1[S:19]([CH3:22])(=[O:21])=[O:20])=[N:7]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:33]=1)=[C:5]([CH3:26])[C:6]([C:13]1[CH:14]=[C:15]([CH:23]([OH:25])[CH3:24])[CH:16]=[CH:17][C:18]=1[S:19]([CH3:22])(=[O:21])=[O:20])=[N:7]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 50906986HCID 50906986, compound

Product 1

HCID 59631308HCID 59631308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The 1-(3-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)-4-(methylsulfonyl)phenyl)ethanone (40 mg, 0.072 mmol) was dissolved in THF (1.00 mL) and cooled to 0° C. To the solution was added 1M lithium aluminum hydride (0.072 mL, 0.072 mmol) in THF and the reaction mixture was allowed to warm to rt over a period of 1.5 h. The reaction was then worked up via the method found in the Fieser and Fieser (Vol. 1) and the mixture was filtered over a short plug of silica gel and washed with EtOAc. The filtrate was cond to give (+/−)-1-(3-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)-quinolin-2-yl)-4-(methylsulfonyl)-phenyl)ethanol. 1H NMR (CDCl3) δ ppm 8.14 (1H, dd, J=8.2, 4.1 Hz), 7.93 (1H, t, J=2.4 Hz), 7.75 (1H, dd, J=4.1, 2.5 Hz), 7.68 (1H, ddd, J=18.5, 8.3, 1.6 Hz), 7.42-7.58 (3H, m), 7.09 (1H, ddd, J=13.4, 8.6, 2.5 Hz), 6.63-6.73 (1H, m), 5.06 (1H, q, J=6.7 Hz), 3.78 (4H, t, J=4.8 Hz), 3.20 (4H, q, J=3.9 Hz), 3.12 (3H, d, J=1.6 Hz), 1.91 (3H, d, J=5.3 Hz), 1.57 (3H, d, J=6.7 Hz). Mass Spectrum (ESI) m/e=555.2 (M+1).

Workup

  1. temperatureto warm to rt over a period of 1.5 h
  2. filtrationthe mixture was filtered over a short plug of silica gel
  3. washwashed with EtOAc

Sources & evidence

ORD record
ord-48aff62f8afe4979bb8c821c706fdf3e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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