Triethylamine → 6-Diethoxyphosphoryl-beta-carboline-3-carboxylic-acid-ethylester

HRID 1903115Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14](I)=[CH:13][CH:12]=3)=[O:5])[CH3:2].[CH2:20]([O:22][P:23]([O-:27])[O:24][CH2:25][CH3:26])[CH3:21].C(N(CC)CC)C>[Pd].CN1CCCC1=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([P:23]([O:24][CH2:25][CH3:26])([O:22][CH2:20][CH3:21])=[O:27])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

1.46 g of 6-iodo-beta-carboline-3-carboxylic-acid-ethylester is added anhydrously to a mixture of 608 g of diethylphosphite, 448 g of triethylamine, 240 mg of palladium tetrakristriphenylphosphine and 60 ml of N-methyl-2-pyrrolidone and is stirred for 12 h at 90° C. After concentration is an oil pump vacuum, the residue is chromatographed on 75 g of silica gel with methylene-chloride/acetone in the ratio of 1/1 as the eluant. The corresponding consolidated fractions are chromatographed on 25 g of silica gel with methylene-chloride/ethanol=10/2 as the eluant. 421 mg of 6-diethoxyphosphoryl-beta-carboline-3-carboxylic-acid-ethylester in the form of an oil is obtained.

Workup

concentrationAfter concentration
customthe residue is chromatographed on 75 g of silica gel with methylene-chloride/acetone in the ratio of 1/1 as the eluant
customThe corresponding consolidated fractions are chromatographed on 25 g of silica gel with methylene-chloride/ethanol=10/2 as the eluant

Sources & evidence

ORD record: ord-71248a9906a94fd99d49915d3f713d54
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04435403

Reaction notes

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