Diethylamine → HCID 46842006, compound

HRID 1846349Notes

Reaction equation

HRID 1846349 reaction equation
CC([O-])(C)C.[Na+].Br[C:8]1[CH:9]=[C:10]([C:14]2[N:23]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:22](=[O:31])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH:11]=[N:12][CH:13]=1.[NH:32]([CH2:35][CH3:36])[CH2:33][CH3:34]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:23]2[C:22](=[O:31])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]2[C:10]2[CH:11]=[N:12][CH:13]=[C:8]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH:9]=2)=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 23676156Sodium t-butoxideHCID 46841857HCID 46841857, compound

Product 1

HCID 46842006HCID 46842006, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

Pd(OAc)2 (0.031 g, 0.14 mmol), DPPF (0.066 g, 0.12 mmol), and NaOtBu (0.059 g, 0.62 mmol) were added to a mixture of 2-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4(3H)-one (0.200 g, 0.48 mmol) and Et2NH (0.07 mL) in toluene (2 mL). The reaction mixture was microwaved at 90° C. and 300 W (max. power) with cooling for 3 hours, before concentration in vacuo. Purification by flash chromatography on silica gel, eluting with 35% to 90% EtOAc in heptane, plus further purification by reverse-phase chromatography, eluting with 10% to 50% CH3CN in H2O, afforded the title compound as a white solid (0.02 g, 10%). 1H-NMR (300 MHz, DMSO-d6): δ8.21 (d, J=6.6 Hz, 1H), 7.88-8.02 (m, 2H), 7.73-7.87 (m, 2H), 7.57-7.70 (m, 1H), 7.36-7.50 (m, 4H), 6.89 (s, 1H), 3.16-3.29 (m, 4H), 0.72-1.11 (m, 6H). MS (APCI) m/z: 405 (M+H)+.

Workup

  1. customThe reaction mixture was microwaved at 90° C.
  2. temperature300 W (max. power) with cooling for 3 hours, before concentration in vacuo
  3. customPurification by flash chromatography on silica gel
  4. washeluting with 35% to 90% EtOAc in heptane, plus further purification by reverse-phase chromatography
  5. washeluting with 10% to 50% CH3CN in H2O

Sources & evidence

ORD record
ord-2541ff3e2b3d4c21b54a1ba8996cbecf
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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