HCID 71237747, compound → HCID 71237731, compound

HRID 2038731Notes

Reaction equation

HRID 2038731 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([F:11])=[CH:5][C:4]=1[C:12]1[CH:20]=[C:19]2[C:15]([C:16]([Sn](C)(C)C)=[N:17][N:18]2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[CH:14][CH:13]=1)[CH3:2].[C:31]([O:35][C:36]([N:38]1[CH2:44][CH2:43][C:42]2[N:45]=[C:46](I)[N:47]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[C:41]=2[CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>C1(C)C=CC=CC=1.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:31]([O:35][C:36]([N:38]1[CH2:44][CH2:43][C:42]2[N:45]=[C:46]([C:16]3[C:15]4[C:19](=[CH:20][C:12]([C:4]5[CH:5]=[C:6]([F:11])[C:7]([O:9][CH3:10])=[CH:8][C:3]=5[CH2:1][CH3:2])=[CH:13][CH:14]=4)[N:18]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:17]=3)[N:47]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[C:41]=2[CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 2

HCID 71237747HCID 71237747, compoundHCID 71237763HCID 71237763, compound

Product 1

HCID 71237731HCID 71237731, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(2-ethyl-5-fluoro-4-methoxy-phenyl)-1-(tetrahydro-pyran-2-yl)-3-trimethylstannanyl-1H-indazole (Preparation 18, 735 mg, 1.53 mmol) in toluene (6 mL) was added 2-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepine-6-carboxylic acid tert-butyl ester (Preparation 29, 829 mg, 1.68 mmol), copper (I) iodide (60 mg, 310 μmol) and tetrakis(triphenylphosphine) palladium(0) (173 mg, 150 μmol). The reaction mixture was degassed with nitrogen, heated at 100° C. for 18 hours, cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 20% EtOAc in toluene to give the title compound as a foam (633 mg) in a 57% yield.

Workup

  1. customThe reaction mixture was degassed with nitrogen
  2. temperaturecooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with 20% EtOAc in toluene

Sources & evidence

ORD record
ord-4993172e82104f8d8ca3a56b710063bd
Source dataset
uspto-grants-2013_11
Patent number
US08575336B2

Reaction notes

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