Triethylamine → [4-(8-Cyclopropyl-2,2,4,4-tetramethyl-chroman-6-yl-ethvnyl)-2-fluorophenyl]acetic acid ethyl ester

HRID 51673Notes

Reaction equation

HRID 51673 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]#[CH:19])[CH:7]=[C:8]3[C:13]=2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]3([CH3:17])[CH3:16])[CH2:3][CH2:2]1.[CH2:20]([O:22][C:23](=[O:33])[CH2:24][C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][C:26]=1[F:32])[CH3:21].C(N(CC)CC)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:20]([O:22][C:23](=[O:33])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:19]#[C:18][C:6]2[CH:7]=[C:8]3[C:13](=[C:4]([CH:1]4[CH2:3][CH2:2]4)[CH:5]=2)[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]3([CH3:17])[CH3:16])=[CH:27][C:26]=1[F:32])[CH3:21]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 18740710Ethyl 2-fluoro-4-iodophenylacetate2×HCID 225690068-Cyclopropyl-6-ethynyl-2,2,4,4-tetramethylchroman2×

Product 1

HCID 69548621[4-(8-Cyclopropyl-2,2,4,4-tetramethyl-chroman-6-yl-ethvnyl)-2-fluorophenyl]acetic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure F and using 8-cyclopropyl-6-ethynyl-2,2,4,4-tetramethylchroman (Intermediate 34, 0.096 g, 0.38 mmol), ethyl-2-fluoro-4-iodo phenyl acetate (Reagent C, 0.104 g, 0.34 mmol), triethyl amine (3 mL), tetrahydrofuran (3 mL), copper(I)iodide (0.020 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.060 g, 0.085 mmol) the title compound was obtained (0.14 g, 85%).

Sources & evidence

ORD record
ord-7db98cb39f884e008bcf02090c977c3c
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

Loading…