3-Methoxyaniline → HCID 46183678, compound

HRID 341302Notes

Reaction equation

HRID 341302 reaction equation
Cl[C:2]1[CH:22]=[N:21][C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH:3]=1)=[CH:11][C:10]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:9][CH:8]=3.CC(C)([O-])C.[Na+].[CH3:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(O)(C)(C)C>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([NH:37][C:2]2[CH:22]=[N:21][C:5]3[NH:6][C:7]4[C:12]([C:4]=3[CH:3]=2)=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=4)[CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 108243-MethoxyanilineHCID 23676156Sodium t-butoxideHCID 46183929HCID 46183929, compound

Product 1

HCID 46183678HCID 46183678, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Procedure

3-chloro-6-(2′-phenylethyl)-9H-pyrido[2,3-b]indole (50 mg, 0.16 mmol, 1 equiv.), Pd2 dba3 (8.2 mg, 0.008 mmol, 0.05 equiv.), 2-Dicyclohexyl phosphino-2′,4′,6′-Triisopropylbiphenyl (L2)(8.1 mg, 0.016 mmol, 0.1 equiv.), sodium tert-butoxide (36 mg, 0.37 mmol, 2.2 equiv.) are introduced in a schlenk tube and flushed with N2. tert-butanol (0.255 ml) and m-Anisidine (25 mg, 0.20 mmol, 1.2 equiv.) are then added. The reaction is carried out at 100° C. overnight and then filtered over celite and evaporated under reduced pressure. The crude product (yellow oil) is purified over silica gel chromatography (eluant AcOEt/PE 4:6, 6:4) to afford the product as a green solid (18 mg, 0.046 mmol) in 29% yield. mp=161-165; IR 3359, 3145, 3022, 1595, 1494, 1467, 1383, 1218, 1151, 1038, 968, 891, 809, 771, 685 cm−1; 1H NMR (300 MHz, CDCl3) 9.94 (br s, 1H, H9), 8.18 (s, 1H, H2), 7.78 (s, 1H, H4), 7.41 (d, 1H, J=8.3 Hz, H8), 7.32-7.14 (m, 71-1, CHPh+CHAn), 6.52 (d, 1H, J=8.1 Hz, H7), 6.47-6.44 (m, 2H, H5+CHPh or CHAn), (br s, 1H, NHAn), 3.77 (s, 3H, OCH3), 3.12-2.97 (m, 4H, 2CH2); MS (+ESI) [M+H+]=394.3

Workup

  1. customflushed with N2
  2. filtrationfiltered over celite
  3. customevaporated under reduced pressure
  4. customThe crude product (yellow oil) is purified over silica gel chromatography (eluant AcOEt/PE 4:6, 6:4)

Sources & evidence

ORD record
ord-20f3df6e310f47a8a0c181796669bc61
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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