Triethylsilane → HCID 118566586, compound

HRID 1056778Notes

Reaction equation

HRID 1056778 reaction equation
[F:1][C:2]1([F:28])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([C:23]4[CH2:27][CH2:26][CH2:25][CH:24]=4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1.C([SiH](CC)CC)C>CO.[Pd]>[F:28][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 118566572HCID 118566572, compound

Product 1

HCID 118566586HCID 118566586, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-chloro-2-cyclopent-1-enyl-quinoline-5-carboxylic acid (4,4-difluoro-cyclo hexyl methyl)-amide (110.00 mg, 0.25 mmol, 1.00 eq) in methanol (15 mL, 136.36 V) was added palladium on carbon (10% w/w) (20 mg, 0.02 mmol, 0.08 eq) under argon atmosphere. Triethylsilane (0.40 mL, 2.49 mmol, 10 eq) was added to the reaction mixture and stirred for 30 min. The reaction mixture was filtered through a Celite bed and the filtrate was concentrated to provide a crude product which was purified by preparative HPLC to afford the title compound (18 mg, 0.04 mmol, 17.5%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.80 (t, J=5.80 Hz, 1H), 7.94-8.01 (m, 2H), 7.75 (d, J=9.01 Hz, 1H), 7.58 (d, J=8.72 Hz, 1H), 3.39-3.40 (m, 1H), 3.27 (t, J=6.21 Hz, 2H), 2.02-2.11 (m, 4H), 1.64-1.86 (m, 11H), 1.27-1.33 (m, 2H). m/z: 407 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered through a Celite bed
  2. concentrationthe filtrate was concentrated
  3. customto provide a crude product which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-61dce2467f444ef8afcb2cdf10310f30
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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