Dimethylformamide → HCID 25120565, compound

HRID 1640928Notes

Reaction equation

HRID 1640928 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20](B5OC(C)(C)C(C)(C)O5)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.Br[C:35]1[CH:40]=[CH:39][N:38]=[C:37]2[NH:41][CH:42]=[CH:43][C:36]=12.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].CN(C=O)C>C(Cl)(Cl)Cl.CC(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:35]5[CH:40]=[CH:39][N:38]=[C:37]6[NH:41][CH:42]=[CH:43][C:36]=56)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:33])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 17749109Barium hydroxide, octahydrateHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 66738069HCID 66738069, compound

Product 1

HCID 25120565HCID 25120565, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
80 °C

Procedure

Combine N-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-4-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-2-yl)pyrimidin-2-amine (0.28 g, 0.6 mmol), 4-bromo-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.51 mmol), barium hydroxide octahydrate (0.48 g, 1.52 mmol), Pd(dppf)Cl2 (40 mg, 0.05 mmol) in 4 mL of mixed solvent of DMF and water (4/1, v/v). Heat the reaction mixture to 80° C. for 45 min. Cool it to RT. Dilute with chloroform/IPA (3:1, v/v) 50 mL. Wash with water and saturated aqueous sodium chloride and dry over magnesium sulfate. Remove the organic solvent to give the crude product. Purify by column chromatography (hexane to ethyl acetate) to afford the title compound (0.17 g, 75%). MS (ES) m/z 457 [M+1]+.

Workup

  1. temperatureCool it to RT
  2. washWash with water and saturated aqueous sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. customRemove the organic solvent
  5. customto give the crude product
  6. customPurify by column chromatography (hexane to ethyl acetate)

Sources & evidence

ORD record
ord-3de2d4c64ee84fb188823c42b0cb19d7
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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