Sodium Carbonate → HCID 68935200, compound

HRID 576277Notes

Reaction equation

HRID 576277 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13]CC)=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.CCO.O.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>[C:20]1([O:19][CH2:18][CH2:17][CH2:16][C:7]2[C:6]3[C:10](=[C:2]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:10][C:6]=4[C:7]#[C:8][CH3:11])[CH:3]=[CH:4][CH:5]=3)[NH:9][C:8]=2[C:11]([OH:13])=[O:12])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 68938945ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Product 1

HCID 68935200HCID 68935200, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

A suspension of EXAMPLE 1C (0.034 g, 0.075 mmol), EXAMPLE 420B (0.1 g, 0.68 mmol), tetrakis(triphenylphosphine)palladium (0.004 g, 0.006 mmol), and solution of Na2CO3 (2M, 0.5 ml, 1 mmol) in dimethoxyethane/EtOH/H2O (7/2/3) 3 mL was heated under microwave conditions at 150 C for 30 min. The reaction mixture was quenched with aq. HCl (1M, 0.4 mL) and product extracted with ethyl acetate (3×7 mL). The organic phases were filtered through a drying cartridge (MgSO4, Alltech Asoc., 2 g) and concentrated under reduced pressure. The crude product was purified by chromatography on SiO2 using 1% AcOH in EtOAc as eluent. 1H NMR (300 MHz, DMSO-d6) δ12.39 (br s, 1H), 10.28 (s, 1H), 8.25 (dd, 1H), 7.87 (d, 1H), 7.71 (d, 1H), 7.38-7.56 (m, 8H), 7.21 (d, 1H), 7.09 (dd, 1H), 6.89 (d, 1H), 4.20 (m, 2H), 3.38 (m, 2H), 2.24 (m, 2H), 1.91 (s, 3H).

Workup

  1. customwas heated under microwave conditions at 150 C for 30 min
  2. customThe reaction mixture was quenched with aq. HCl (1M, 0.4 mL) and product
  3. extractionextracted with ethyl acetate (3×7 mL)
  4. filtrationThe organic phases were filtered through a drying cartridge (MgSO4, Alltech Asoc., 2 g)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by chromatography on SiO2 using 1% AcOH in EtOAc as eluent

Sources & evidence

ORD record
ord-b5485f6e33ea40d08831152d0a5a6834
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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