Sodium Carbonate → HCID 59379882, compound

HRID 2353719Notes

Reaction equation

HRID 2353719 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][S:9]([CH2:12][CH2:13][OH:14])(=[O:11])=[O:10])[CH:5]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[N:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.O.C(O)C.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>[NH2:34][C:33]1[CH:35]=[CH:36][C:30]([C:2]2[N:7]=[C:6]([CH2:8][S:9]([CH2:12][CH2:13][OH:14])(=[O:11])=[O:10])[CH:5]=[C:4]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]3[CH3:21])[N:3]=2)=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380137HCID 59380137, compound

Product 1

HCID 59379882HCID 59379882, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
80 °C

Procedure

trans-Dichlorobis(triphenylphosphine)palladium (II) (0.013 g, 0.02 mmol) was added to 2-[[2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfonyl]ethanol (0.122 g, 0.36 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.119 g, 0.54 mmol) and sodium carbonate (0.908 mL, 1.82 mmol) in 18% DMF in a mixture of DME:water:ethanol (7:3:2) (10 mL) at RT under nitrogen. The resulting solution was stirred at 80° C. for 2 hours. The reaction was cooled and partitioned between ethyl acetate and water. The reaction mixture was extracted with ethyl acetate twice and the combined organics dried (MgSO4) filtered and concentrated in vacuo to give the desired (0.143 g).

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate and water
  3. extractionThe reaction mixture was extracted with ethyl acetate twice
  4. dry with materialthe combined organics dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the

Sources & evidence

ORD record
ord-a30b4d24207344e3982f3715eef0f791
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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