Aniline → 6,6-Dimethyl-3-phenylamino-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one

HRID 1937633Notes

Reaction equation

HRID 1937633 reaction equation
Br[C:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[CH3:12][C:7]1([CH3:13])[CH2:6][C:5]2[N:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:3]=[C:2]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[C:9](=[O:11])[CH2:8]1

Participants

5

Reactant 3

HCID 6115AnilineHCID 224612763-Bromo-6,6-dimethyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 224612846,6-Dimethyl-3-phenylamino-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-oneYield 43.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-bromo-6,6-dimethyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one (50 mg, 0.16mmol), aniline (17 μL, 0.19 mmol), sodium tert-butoxide (18 mg, 0.19 mmol) tris(dibenzylideneacetone)dipalladium (7.2 mg, 0.008mmol) and (R)-(+)-2,2′-bis(diphenylphosphino)-1,1-binaphthyl (9.8 mg, 0.016 mmol) in toluene (3 mL) was heated at reflux for 3 h. The toluene was evaporated and the residue chromatographed on silica gel, eluting with isohexane: EtOAc (9:1→4:1). The title compound (23 mg, 43%) was isolated as a yellow solid. mp 135-138° C. Found: C, 73.98; H, 6.10; N, 12.33%. C21H21N3O0.0.45(H2O): C,74.29; H, 6.50; N, 12.38%. 1H NMR (360 MHz, d6-DMSO) δ 1.07 (6H,s), 2.37 (2H,s), 3.03 (2H,s), 6.81 (1H,t, J=7.4 Hz), 7.08 (2H,d, J=7.7 Hz), 7.25-7.29 (2H,m), 7.41 (1H,dd, J=7.2 and and 4.9Hz), 7.72 (1H,d, J=8.1 Hz), 8.01 (1H,d of t, J=7.6 and 1.8 Hz), 8.16 (1H,s), 8.57-8.60 (1H,m). MS (ES+) 332 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customThe toluene was evaporated
  4. customthe residue chromatographed on silica gel
  5. washeluting with isohexane: EtOAc (9:1→4:1)

Sources & evidence

ORD record
ord-c6a2e9caf0fb405cb0ff4e893472f404
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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