Methanol → 6-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

HRID 658069Notes

Reaction equation

HRID 658069 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[C:15]([F:34])=[CH:16][C:17]([N+:31]([O-])=O)=[C:18]([CH:20]=[C:21]([CH2:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:22]#[N:23])[CH:19]=2)[CH:10]=[CH:11][CH:12]=1.[NH4+].[Cl-].CO>[Zn].C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[CH:19]=[C:18]3[C:17](=[CH:16][C:15]=2[F:34])[N:31]=[C:22]([NH2:23])[C:21]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:20]3)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 68738694HCID 68738694, compound

Product 1

HCID 687389956-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In three μwave tubes 3-[5-(3-[1,3]dioxan-2-yl-phenylsulfanyl)-4-fluoro-2-nitro-phenyl]-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile (0.25 g, 0.52 mmol, each tube), Zn (3 g, 0.046 mol, each tube), NH4Cl (0.98 g, 0.018 mol, each tube), CH3OH (3 mL, in each tube), and THF (1 mL, in each tube) were reacted via μwave @ 300W, 130° C. for 12 min. The resulting mixtures were combined, filtered through Celite®, and the solvent removed to yield a residue, which was purified by silica column chromatography (50% EtOAc/heptanes) to yield a solid.

Workup

  1. filtrationfiltered through Celite®
  2. customthe solvent removed
  3. customto yield a residue, which
  4. customwas purified by silica column chromatography (50% EtOAc/heptanes)
  5. customto yield a solid

Sources & evidence

ORD record
ord-65c31851912e429fa3e31cf51ac7d68f
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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