Potassium Phosphate, Tribasic → HCID 11209970, compound

HRID 495216Notes

Reaction equation

HRID 495216 reaction equation
[CH2:1]([C:3]1[C:7](I)=[C:6]([CH:9]=[O:10])[NH:5][C:4]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[CH:28]=[C:27]1B(O)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(COC)OC>[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[CH:28]=[C:27]1[C:7]1[C:3]([CH2:1][CH3:2])=[C:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[NH:5][C:6]=1[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2776266Benzo[b]furan-2-boronic acidHCID 11348633HCID 11348633, compound

Product 1

HCID 11209970HCID 11209970, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Tert-butyl 3-ethyl-5-formyl-4-iodo-1H-pyrrole-2-carboxylate was obtained following the procedures described in Example 1. To a mixture of tert-butyl 3-ethyl-5-formyl-4-iodo-1H-pyrrole-2-carboxylate (0.0597 g, 0.172 mmol), K3PO4 (0.180 g, 0.85 mmol), Pd(PPh3)4(0.0120 g, 0.010 mmol), and 1-benzofuran-2-ylboronic acid (0.0330 g, 0.21 mmol) under N2 was added dimethoxyethane (2.5 mL). The reaction was heated to 85° C. and refluxed for 5 h. After cooling to ambient temperature, the reaction was filtrated through a pad of silica gel and concentration. The resultant residue was purified by normal phase chromatography (5-15% ethyl acetate/hexanes). Proton NMR for the product was consistent with the title compound as a 2:1 mixture of atropdiastereomers. 1H NMR (500 MHz, CDCl3) δ 10.17 (s, 0.7 H); 9.59 (s, 0.3H); 7.64 (app. d, J=7.6 Hz, 1H); 7.52 (app. d, J=8.1 Hz, 1H); 7.34 (app. t, J=7.7 Hz, 1H); 7.28 (app. t, J=7.6 Hz, 1H), 6.92 (s, 0.7H); 6.80 (s, 0.3H); 3.00 (q, J=7.3 Hz, 1.4H); 2.79 (q, J=7.5 Hz, 0.6H); 1.62 (s, 6.3H); 1.59 (s, 2.7H); 1.28 (t, J=7.3 Hz, 2.1H); 1.23 (t, J=7.6 Hz, 0.9H). HRMS (ES) exact mass calculated for C20H21NNaO4 (M+Na+): 362.1362. Found 362.1362.

Workup

  1. temperaturerefluxed for 5 h
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe reaction was filtrated through a pad of silica gel and concentration
  4. customThe resultant residue was purified by normal phase chromatography (5-15% ethyl acetate/hexanes)
  5. additionProton NMR for the product was consistent with the title compound as a 2:1 mixture of atropdiastereomers

Sources & evidence

ORD record
ord-c69eda17f6554a5c961735bbdb0f212e
Source dataset
uspto-grants-2009_05
Patent number
US07538231B2

Reaction notes

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