Diethylamine → HCID 46841558, compound

HRID 1846338Notes

Reaction equation

HRID 1846338 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]([CH2:26][CH3:27])[CH3:25])=[CH:20][CH:19]=3)[C:16](=[O:28])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.CC([O-])(C)C.[Na+].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>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:24]([C:21]1[CH:22]=[CH:23][C:18]([N:17]2[C:16](=[O:28])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=[C:8]2[C:5]2[CH:6]=[N:7][C:2]([N:37]([CH2:38][CH3:39])[CH2:35][CH3:36])=[CH:3][CH:4]=2)=[CH:19][CH:20]=1)([CH2:26][CH3:27])[CH3:25]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 23676156Sodium t-butoxideHCID 46841556HCID 46841556, compound

Product 1

HCID 46841558HCID 46841558, compoundYield 37.1%

Reagents, catalysts & solvents 3

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

Procedure

2-(6-bromopyridin-3-yl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one (0.110 g, 0.253 mmol), Pd(OAc)2 (0.017 g, 0.076 mmol), DPPF (0.035 g, 0.063 mmol), NaOt-Bu (0.032 g, 0.330 mmol), and diethylamine (0.040 mL, 0.385 mmol) were combined in toluene (2 mL) in a microwave tube under nitrogen. The mixture was microwaved at 90° C., 300 W, for 3 hours. The mixture was concentrated and purified by flash chromatography on silica gel, eluting with 30% ethyl acetate/heptane to 100% ethyl acetate, to afford the title compound as a white solid (0.040 g, 37%). 1H-NMR (300 MHz, DMSO-6): δ 8.14-8.17 (m, 1H), 8.02 (d, J=2.3 Hz, 1H), 7.84-7.90 (m, 1H), 7.73 (d, J=7.8 Hz, 1H), 7.52-7.57 (m, 1H), 7.32-7.35 (m, 1H), 7.18-7.28 (m, 4H), 6.33 (d, J=9.1 Hz, 1H), 3.41 (q, J=6.9 Hz, 4H), 2.57-2.64 (m, 1H), 1.41-1.62 (m, 2H), 1.19 (d, J=6.9 Hz, 3H), 1.01 (t, J=6.9 Hz, 6H), 0.67 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 427 (M+H)+.

Workup

  1. customThe mixture was microwaved at 90° C.
  2. concentrationThe mixture was concentrated
  3. custompurified by flash chromatography on silica gel
  4. washeluting with 30% ethyl acetate/heptane to 100% ethyl acetate

Sources & evidence

ORD record
ord-65af80a8b60c492ea002107dafa3672e
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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