Diethylamine → HCID 46841858, compound

HRID 1846347Notes

Reaction equation

HRID 1846347 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]([CH:30]([CH2:32][CH3:33])[CH3:31])=[CH:26][CH:25]=3)[C:22](=[O:34])[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:35]([CH2:38][CH3:39])[CH2:36][CH3:37]>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]>[CH:30]([C:27]1[CH:28]=[CH:29][C:24]([N:23]2[C:22](=[O:34])[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:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[CH:9]=2)=[CH:25][CH:26]=1)([CH2:32][CH3:33])[CH3:31]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 23676156Sodium t-butoxideHCID 46841856HCID 46841856, compound

Product 1

HCID 46841858HCID 46841858, compoundYield 5.9%

Reagents, catalysts & solvents 3

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

Procedure

Pd(OAc)2 (0.026 g, 0.12 mmol), DPPF (0.055 g, 0.10 mmol) and NaOtBu (0.049 g, 0.52 mmol) were added to a mixture of 2-(5-bromopyridin-3-yl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one (0.175 g, 0.40 mmol) and Et2NH (0.06 mL, 0.60 mmol) in toluene (2 mL). The mixture was microwaved at 90° C. and 300 W (max. power) with cooling for 3 hours, before being concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% to 60% EtOAc in heptane, plus further purification by flash chromatography on silica gel, eluting with 30% to 90% EtOAc in heptane, afforded the title compound as a white solid (0.010 g, 5%). 1H-NMR (300 MHz, DMSO-d6): δ8.20 (d, J=6.9 Hz, 1H), 7.84-7.98 (m, 3H), 7.77 (d, J=7.9 Hz, 1H), 7.55-7.68 (m, 1H), 7.26 (d, J=7.8 Hz, 2H), 7.08-7.20 (m, 2H), 6.80 (s, 1H), 3.06-3.23 (m, 4H), 2.51-2.65 (m, 1H), 1.35-1.60 (m, 2H), 1.08-1.20 (m, 3H), 0.81-1.00 (m, 6H), 0.62 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 427 (M+H)+.

Workup

  1. customThe mixture was microwaved at 90° C.
  2. temperature300 W (max. power) with cooling for 3 hours
  3. concentrationbefore being concentrated in vacuo
  4. customPurification by flash chromatography on silica gel
  5. washeluting with 5% to 60% EtOAc in heptane, plus further purification by flash chromatography on silica gel
  6. washeluting with 30% to 90% EtOAc in heptane

Sources & evidence

ORD record
ord-eeae9a8926f444a9ba91cf51ce69cf5a
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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