Diisopropylamine → HCID 58886657, compound

HRID 494717Notes

Reaction equation

HRID 494717 reaction equation
C1COCC1.C(NC(C)C)(C)C.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].[CH3:19][O:20][C:21]([C:23]1[C:24]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=2[F:42])=[C:25]([F:33])[C:26]2[N:27]([C:29](I)=[CH:30][N:31]=2)[CH:28]=1)=[O:22]>C(OCC)(=O)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>[CH3:19][O:20][C:21]([C:23]1[C:24]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=2[F:42])=[C:25]([F:33])[C:26]2[N:27]([C:29]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:30][N:31]=2)[CH:28]=1)=[O:22]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 66111TrimethylsilylacetyleneHCID 58886665HCID 58886665, compound

Product 1

HCID 58886657HCID 58886657, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

THF (1.0 mL), diisopropylamine (95 μL, 0.68 mmol) and trimethylsilylacetylene (38 μL, 0.27 mmol) were added to a mixture of 8-fluoro-7-(2-fluoro-4-methylphenylamino)-3-iodo-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (100 mg, 0.23 mmol), CuI (4.0 mg, 0.023 mmol) and PdCl2(PPh3)2 (16 mg, 0.023 mmol). The solution was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate, washed with saturated NaHCO3 (3×), brine (2×), dried over Na2SO4 and concentrated to a dark brown solid. Flash column chromatography (40:1 dichloromethane/MeOH) provide desired product (30 mg, 32%) as a yellow liquid. MS APCI (+) m/z 414 (M+1) detected. 1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1H), 8.61 (s, 1H), 7.80 (s, 1H), 6.90 (m, 3H), 4.00 (s, 3H), 2.32 (s, 3H), 0.33 (s, 9H). 19F NMR (376 MHz, CDCl3)−129.12 (s, 1F), −141.99 (s, 1F).

Workup

  1. washwashed with saturated NaHCO3 (3×), brine (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to a dark brown solid

Sources & evidence

ORD record
ord-cae4f9f62aa3480c8d84cd05236e761b
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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