Diisopropylamine → HCID 69074066, compound

HRID 1820993Notes

Reaction equation

HRID 1820993 reaction equation
[F:1][C:2]1([F:35])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][C:19]=4[CH3:33])[N:14]=3)=[CH:9][C:8]=2I)[CH2:3]1.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38].C(NC(C)C)(C)C>O1CCOCC1.[Cu](I)I.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[F:1][C:2]1([F:35])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][C:19]=4[CH3:33])[N:14]=3)=[CH:9][C:8]=2[C:41]#[C:40][Si:37]([CH3:39])([CH3:38])[CH3:36])[CH2:3]1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 69068501HCID 69068501, compound

Product 1

HCID 69074066HCID 69074066, compoundYield 75.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 61 mg (0.10 mmol) of tert-butyl 3-(4-(5-(6-(3,3-difluoropyrrolidin-1-yl)-5-iodopyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate (from EXAMPLE 34) in 5.0 mL of 1,4-dioxane were added 1 mg (0.005 mmol) of copper(II) iodide, 20 mg (0.21 mmol) of (trimethylsilyl)acetylene, 12 mg (0.12 mmol) of diisopropylamine, and 2.6 mg (0.005 mmol) of bis(tri-tert-butylphosphine)palladium(0). The mixture was stirred at rt for 16 h and concentrated. Chromatography on a Biotage 25S cartridges using 9:1 v/v hexanes/EtOAc as the eluant afforded 43 mg of a yellow solid as the title compound: 1HNMR (500 MHz, CDCl3) δ 0.26 (s, 9H), 1.45 (s, 9H), 2.46 (m, 2H), 2.58 (t, J=7.8, 2H), 2.66 (s, 3H), 2.96 (t, J=7.8, 2H), 4.15 (t, J=7.3, 2H), 4.32 (t, J=13, 2H), 7.18 (s, 1H), 7.19 (s, 1H), 8.01 (m, 1H), 8.34 (d, J=2.3, 1H), 8.88 (d, J=2.3, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-5e5e1b121c6c440caafe7039fcc8fb6c
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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