Sodium Carbonate → HCID 24936343, compound

HRID 422114Notes

Reaction equation

HRID 422114 reaction equation
[F:1][C:2]1[C:3]([C:17]2[S:21][C:20]3[C:22](B4OC(C)(C)C(C)(C)O4)=[CH:23][CH:24]=[CH:25][C:19]=3[CH:18]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[N:6][CH:7]=1.[F:35][C:36]1[N:41]=[CH:40][C:39]([CH2:42][OH:43])=[C:38](I)[CH:37]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(Cl)(Cl)Cl.C(O)(C)C>[F:1][C:2]1[C:3]([C:17]2[S:21][C:20]3[C:22]([C:38]4[C:39]([CH2:42][OH:43])=[CH:40][N:41]=[C:36]([F:35])[CH:37]=4)=[CH:23][CH:24]=[CH:25][C:19]=3[CH:18]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 666734811-(2-{5-Fluoro-4-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophen-2-yl]-pyrimidin-2-ylamino}-ethyl)-imidazolidin-2-oneHCID 66674391HCID 66674391, compound

Product 1

HCID 24936343HCID 24936343, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
100 °C

Procedure

Combine 1-(2-{5-fluoro-4-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophen-2-yl]-pyrimidin-2-ylamino}-ethyl)-imidazolidin-2-one (120 mg, 0.25 mmol), (6-fluoro-4-iodo-pyridin-3-yl)-methanol (100 mg; 0.32 mmol), (1,1′-bis(di-phenylphosphino)ferrocene)palladium(II) chloride (10.14 mg; 0.01 mmol), 2-(di-tert-butylphosphino)biphenyl (2 mg, 0.01 mmol) and sodium carbonate (2 M, 0.2 mL, 0.4 mmol) in 5 mL of dioxane in a pressure tube. Heat the mixture at 100° C. overnight in oil bath. Cool the mixture down to room temperature, dilute it with chloroform-isopropyl alcohol (3/1). Wash the organic phase with saturated aqueous sodium chloride, dry it over sodium sulfate and concentrate it to an oily residue. Purify the crude by flash column chromatography (10% methanol in dichloromethane) to afford the title compound (25 mg, 21%). MS (ES) m/z 483 [M+1]+.

Workup

  1. temperatureCool the mixture down to room temperature
  2. washWash the organic phase with saturated aqueous sodium chloride
  3. dry with materialdry it over sodium sulfate
  4. concentrationconcentrate it to an oily residue
  5. customPurify the crude by flash column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8eafebf2920d46d4bc149d2e53ac286c
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

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