Water → [3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester

HRID 1784843Notes

Reaction equation

HRID 1784843 reaction equation
[CH3:1][O:2][C:3](=[O:38])[NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[Si](C(C)C)(C(C)C)C(C)C)[CH:8]=[C:7]([C:30]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[O:31])[CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:38])[NH:4][C:5]1[CH:6]=[C:7]([C:30]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[O:31])[CH:8]=[C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 50994359[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester

Product 1

HCID 15602991[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 0.160 g (0.31 mmol) of [3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-carbamic acid methyl ester in 5 mL of THF was added 0.310 mL of 1M tetra-n-butylammonium fluoride in THF. The reaction was stirred 10 min, poured into water and ethyl acetate. The phases were separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium bicarbonate and brine and dried over sodium sulfate, and the volatiles were removed under reduced pressure. The crude product was chromatographed using 1-5% methanol/chloroform to give [3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-carbamic acid methyl ester. 1H NMR (400 MHz, methanol-d4): δ 9.08 (s, 1H), 8.79 (d, J=3.9 Hz, 1H), 8.43 (s, 1H), 8.16 (d, J=7.8 Hz, 1H), 8.08 (s, 1H), 7.81 (s, 1H), 7.78 (s, 1H), 7.38-7.46 (m, 2H), 7.22-7.27 (m, 2H), 7.19 (d, J=7.0 Hz, 1H), 7.01 (s, 1H), 6.72 (s, 1H), 3.79 (s, 3H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customthe volatiles were removed under reduced pressure
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-3bd3a8925f5747e98eebb13938d740d2
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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