Diisopropylamine → HCID 69005612, compound

HRID 2102417Notes

Reaction equation

HRID 2102417 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:9]([F:19])[C:8]([Cl:20])=[C:7](Cl)[N:6]=1)=[O:4].[Si:22]([C:26]#[CH:27])([CH3:25])([CH3:24])[CH3:23].N(C(C)C)C(C)C>C1COCC1.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.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:9]([F:19])[C:8]([Cl:20])=[C:7]([C:27]#[C:26][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 86599611HCID 86599611, compound

Product 1

HCID 69005612HCID 69005612, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 5,6-dichloro-4-fluoro-3-(2-fluorophenylamino)-pyridine-2-carboxylic acid methyl ester (1.00 equivalent), TMS-acetylene (1.20 equivalents), Pd(PPh3)2Cl2 (0.10 equivalents), CuI (0.10 equivalents), and i-Pr2NH (2.00 equivalents) in THF is stirred for 16 hours at room temperature. THF is evaporated in vacuo. The reaction mixture is diluted with EtOAc and washed with saturated aqueous NH4Cl and brine. The organic layer is dried over MgSO4, filtered, and concentrated to give the crude material that is purified by flash column chromatography to afford the desired product.

Workup

  1. customTHF is evaporated in vacuo
  2. additionThe reaction mixture is diluted with EtOAc
  3. washwashed with saturated aqueous NH4Cl and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude material that
  8. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-ca4309342a904a64b0d26bfba207ce0e
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

Loading…