Triphenylphosphine → methyl 5-{[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]oxy}-1H-indole-2-carboxylate

HRID 1874789Notes

Reaction equation

HRID 1874789 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:46][C:47]1([CH3:55])[O:52][CH2:51][CH:50]([CH2:53]O)[CH2:49][O:48]1>C(Cl)Cl>[CH3:46][C:47]1([CH3:55])[O:52][CH2:51][CH:50]([CH2:53][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:5]3)[CH2:49][O:48]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 21904362methyl 5-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 59451360methyl 5-{[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]oxy}-1H-indole-2-carboxylateYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 5-Hydroxy-1H-indole-2-carboxylate (0.10 g, 0.5 mmol), triphenylphosphine (0.28 g, 1.0 mmol), diethyl azodicarboxylate (0.18 g, 1.0 mmol) and (2,2-dimethyl-1,3-dioxan-5-yl)methanol (0.15 g, 1.0 mmol) were dissolved in CH2Cl2 (5 mL) and the mixture was stirred overnight. The solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were neutralized with saturated NaHCO3 and extracted with EtOAc. The organic extracts were combined dried over Na2SO4, filtered and evaporated to afford the title compound (0.15 g, 90%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.74 (br. s., 1H), 7.29 (d, 1H), 7.09 (d, 1H), 7.01 (d, 1H), 6.88 (dd, 1H), 3.92-4.01 (m, 4H), 3.81 (s, 3H), 3.72 (dd, 2H), 1.97-2.08 (m, 1H), 1.31 (s, 3H), 1.28 (s, 3H). MS: m/z 342.2 (M+23).

Workup

  1. customThe solvent was evaporated
  2. customPurification
  3. extractionextracted with EtOAc
  4. dry with materialThe organic extracts were combined dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-bdf74f0af1ba40a5a3fb1d0cdcebe4b8
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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