Diethylamine → HCID 46841557, compound

HRID 1846337Notes

Reaction equation

HRID 1846337 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]([Cl:24])=[CH:20][CH:19]=3)[C:16](=[O:25])[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+].[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>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:24][C:21]1[CH:22]=[CH:23][C:18]([N:17]2[C:16](=[O:25])[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:34]([CH2:35][CH3:36])[CH2:32][CH3:33])=[CH:3][CH:4]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 8021Diethylamine2×HCID 23676156Sodium t-butoxideHCID 46841555HCID 46841555, compound

Product 1

HCID 46841557HCID 46841557, compoundYield 49.4%

Reagents, catalysts & solvents 3

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

Procedure

2-(6-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4(3H)-one (0.035 g, 0.085 mmol), Pd(OAc)2 (0.002 g, 0.009 mmol), DPPF (0.004 g, 0.007 mmol), NaOt-Bu (0.011 g, 0.110 mmol), and diethylamine (0.020 mL, 0.19 mmol) were combined in toluene (2 mL) in a microwave tube under nitrogen. The mixture was microwaved at 80° C., 300 W, for 30 minutes. Additional diethylamine (0.040 mL, 0.38 mmol) was added and the microwaving was continued at 90° C. for 2.5 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 (0.017 g, 49%). 1H-NMR (300 MHz, DMSO-6): δ 8.14-8.17 (m, 1H), 8.08 (d, J=2.8 Hz, 1H), 7.85-7.91 (m, 1H), 7.73 (d, J=7.8 Hz, 1H), 7.35-7.58 (m, 6H), 6.43 (d, J=9.0 Hz, 1H), 3.44 (q, J=7.0 Hz, 4H), 1.05 (t, 6.9 Hz, 6H). MS (APCI) m/z: 405 (M+H)+.

Workup

  1. customThe mixture was microwaved at 80° C.
  2. waitthe microwaving was continued at 90° C. for 2.5 hours
  3. concentrationThe mixture was concentrated
  4. custompurified by flash chromatography on silica gel
  5. washeluting with 30% ethyl acetate/heptane to 100% ethyl acetate

Sources & evidence

ORD record
ord-96309ce5fa6646608bdcd1e5d86cbafc
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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