4-Hydroxymethylpyridine → ethyl 6-trimethylsilyl-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate

HRID 1948795Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([CH2:7]O)=[CH:3][CH:2]=1.C(C=P(CCCC)(CCCC)CCCC)#N.[CH3:25][Si:26]([CH3:42])([CH3:41])[C:27]1[CH:35]=[C:34]2[C:30]([CH:31]=[C:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[NH:33]2)=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[CH3:25][Si:26]([CH3:41])([CH3:42])[C:27]1[CH:35]=[C:34]2[C:30]([CH:31]=[C:32]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:33]2[CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

0.42 g (3.82 mmol) of 4-pyridinylmethanol and 0.92 g (3.826 mmol) of (cyano-methylene)tributylphosphorane (CMBP) are added, at ambient temperature, to a solution of 0.5 g (1.91 mmol) of ethyl 6-trimethylsilyl-1H-indole-2-carboxylate, obtained according to the protocol described in stage 1.2, in 8 ml of dry toluene, maintained under an inert atmosphere. The reaction mixture is stirred at 110° C. for 15 hours and then concentrated to dryness. The reaction crude is subsequently purified by flash chromatography on a silica gel column, elution being carried out with a mixture of heptane and ethyl acetate, to give 0.644 g of the expected ethyl 6-trimethylsilyl-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate in the form of a yellow solid.

Workup

customobtained
temperaturemaintained under an inert atmosphere
concentrationconcentrated to dryness
customThe reaction crude
customis subsequently purified by flash chromatography on a silica gel column, elution
additionbeing carried out with a mixture of heptane and ethyl acetate

Sources & evidence

ORD record: ord-6a1fce01fcce4e0b9c1a69774219b3e5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399491B2

Reaction notes

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