Isopropylbenzylamine → HCID 58168247, compound

HRID 1029270Notes

Reaction equation

HRID 1029270 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[CH2:17]([NH:24][CH:25]([CH3:27])[CH3:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>O1CCOCC1.CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:17]([N:24]([CH:25]([CH3:27])[CH3:26])[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 66024IsopropylbenzylamineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168247HCID 58168247, compoundYield 7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

6 (200 mg, 0.87 mmol), N-benzylpropan-2-amine (0.58 mL, 3.47 mmol), Pd(OAc)2 (8 mg, 0.03 mmol), X-Phos (33 mg, 0.07 mmol), and NaOtBu (250 mg, 2.6 mmol) were suspended in dioxane (3 mL), and stirred for 5 minutes at 150° C. via microwave. The reaction solution was diluted with DMSO and filtered. The crude product was purified directly via prep-LC-MS to provide 448 (21 mg, 7% yield) as a white powder. LC-MS (M+H=344, obsd.=344). 1H NMR (400 MHz, DMSO-D6) δ 11.45 (m, 1H), 8.53 (m, 1H), 8.38 (m, 1H), 8.00 (s, 1H), 7.49 (m, 1H), 7.32 (m, 5H), 7.18 (m, 1H), 7.00 (m, 1H), 4.66 (s, 2H), 1.25 (d, J=6.6, 6H), 0.84 (m, 1H).

Workup

  1. filtrationfiltered
  2. customThe crude product was purified directly via prep-LC-MS

Sources & evidence

ORD record
ord-241e20053bec4d0d897cef55de500381
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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