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

HRID 2185242Notes

Reaction equation

HRID 2185242 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-f0bfbac6d190418abe9e4f6d0961e7c1
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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