Dimethylamine → HCID 46842452, compound

HRID 1846372Notes

Reaction equation

HRID 1846372 reaction equation
[CH3:1][NH:2][CH3:3].Br[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27](C(OC(C)(C)C)=O)[CH:26]=[CH:25]3)=[CH:7][CH:6]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:3])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[CH:25]3)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 67455020HCID 67455020, compound

Product 1

HCID 46842452HCID 46842452, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Dimethylamine (0.3 mL, 0.58 mmol) was added to a solution of tert-butyl 5-(3-(4-bromophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-1-carboxylate (0.200 g, 0.38 mmol), NatOBu (0.112 g, 1.20 mmol), Pd(OAc)2 (0.013 g, 0.06 mmol) and (t-Bu)3PHBF4 (0.034 g, 0.12 mmol) were added to toluene (5 mL). The mixture was microwaved at 300 W (max. power) and 90° C. for 30 min, before the mixture was concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 20% to 60% EtOAc in hexanes, afforded the title compound as a brown-yellow solid (0.048 g, 33%). 1H-NMR (300 MHz, DMSO-d6): δ11.14 (s, 1H), 8.16 (d, J=7.7 Hz, 1H), 7.83-7.88 (m, 1H), 7.67-7.73 (m, 2H), 7.52-7.57 (m, 1H), 7.33 (s, 1H), 7.18 (d, J=8.7 Hz, 1H), 7.03-7.08 (m, 3H), 6.54 (d, J=8.8 Hz, 2H), 6.39 (s, 1H), 2.83 (s, 6H). MS (APCI) m/z: 381 (M+H)+.

Workup

  1. customThe mixture was microwaved at 300 W (max. power) and 90° C. for 30 min, before the mixture
  2. concentrationwas concentrated in vacuo
  3. customPurification by flash chromatography on silica gel
  4. washeluting with 20% to 60% EtOAc in hexanes

Sources & evidence

ORD record
ord-92364c4704274259b32f1de220bcc019
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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