Sodium Carbonate → HCID 69231128, compound

HRID 915350Notes

Reaction equation

HRID 915350 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10](Br)=[C:9]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([C:33]2[CH:34]=[CH:35][C:30]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:31][CH:32]=2)=[C:9]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 69231351HCID 69231351, compound

Product 1

HCID 69231128HCID 69231128, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of ethyl 1-benzyl-3-bromo-5-nitro-1H-indole-2-carboxylate (0.40 g, 1 mmol), 4-tert-butylbenzeneboronic acid (0.36 g, 2 mmol), 2 M aqueous sodium carbonate (5 mL), tetrakis(triphenylphosphine)palladium (0) (0.20 g, 0.17 mmol) in ethanol (5 mL) and toluene (5 ml) was heated at 65° C. for 16 h and then cooled. The reaction mixture was diluted with 1 N hydrochloric acid and then extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and concentrated. Flash silica gel chromatography using 5˜25% ethyl acetate/hexane gave 0.41 g (90%) of ethyl 1-benzyl-3-(4-tert-butylphenyl)-5-nitro-1H-indole-2-carboxylate as a yellowish solid: 1H NMR (DMSO-d6) δ 0.92 (t, J=7.0 Hz, 3 H), 1.36 (s, 9 H),4.10 (q, J=7.0 Hz, 2 H), 5.89 (s, 2H), 7.09 (d, J=8.4 Hz, 2 H), 7.22-7.45 (m, 3 H), 7.95 (d, J=7.6 Hz, 2 H), 7.54 (d, J=8.5 Hz, 2 H), 7.91 (d, J=11.2 Hz, 1H), 8.22 (dd, J=11.2, 2.1 Hz, 1 H), 8.37 (d, J=2.1 Hz, 1 H); MS (ESI) m/z 457 (MH+); HRMS calcd for C29H29N2O4: 457.2128; found (ESI+): 457.2114; Anal. calcd for C28H28N2O4: C, 73.66; H, 6.18; N, 6.14. Found: C, 73.48; H, 6.30; N, 5.97.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-36551106bb204659a0051776924f6308
Source dataset
uspto-grants-2007_09
Patent number
US07265148B2

Reaction notes

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