Triethylamine → 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)pent-4-ynoic acid

HRID 2190155Notes

Reaction equation

HRID 2190155 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:23][C:11]3=[N:12][C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:14](I)[CH:15]=[C:10]3[C:9]=2[C:24]([NH:26][CH3:27])=[O:25])=[CH:4][CH:3]=1.[C:28]([OH:34])(=[O:33])[CH2:29][CH2:30][C:31]#[CH:32].C(N(CC)CC)C>[Cu]I.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:23][C:11]3=[N:12][C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([C:32]#[C:31][CH2:30][CH2:29][C:28]([OH:34])=[O:33])[CH:15]=[C:10]3[C:9]=2[C:24](=[O:25])[NH:26][CH3:27])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 224644-Pentynoic acidHCID 545750872-(4-fluorophenyl)-5-iodo-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 580525425-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)pent-4-ynoic acid

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(4-fluorophenyl)-5-iodo-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide (52 mg), pent-4-ynoic acid (51 mg), triethylamine (0.43 ml), copper(I) iodide (0.79 mg), Pd(PPh3)Cl2 (5.8 mg) and THF (1.4 ml) was bubbled with nitrogen. Heated at 80° C. for 16 h. Cooled to rt and purified by preparative HPLC. (M+H)+=474.1; Retention time=1.22 min, Method A.

Workup

  1. customwas bubbled with nitrogen
  2. temperatureCooled to rt
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1b789dcc88b64b449680617252d144eb
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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