Tetrahydrofuran → HCID 67052806, compound

HRID 1943934Notes

Reaction equation

HRID 1943934 reaction equation
[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6]C1C=C2C(I)=NN(CC3C=CC(OC)=CC=3)C2=NC=1)=[O:5].C(N(CC)CC#C)C.C(N(CC)CC)C.C1COCC1>[Cl-].[Na+].O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:32])=[O:33])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 20010DietylaminopropinHCID 67088944HCID 67088944, compound

Product 1

HCID 67052806HCID 67052806, compoundYield 264.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

2,6-Difluoro-N-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (100 mg, 0.156 mmol), N,N-diethylprop-2-yn-1-amine (19.1 mg, 0.172 mmol), triethylamine (212.6 μL 1.56 mmol), copper(I) iodide (1.19 mg, 0.00624 mmol) and THF (10 mL) were added to a 100 mL round-bottomed flask. Next, Pd(PPh3)4 (7.21 mg, 0.00624 mmol) was added under nitrogen. The mixture was heated to 50° C. for 24 hours. The mixture was cooled to room temperature and diluted with brine (50 mL). The mixture was extracted with EtOAc (50 mL), dried with sodium sulfate, filtered and concentrated to get N-(3-(3-(diethylamino)prop-1-ynyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3, 4-1)]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (115 mg, 88%) as a solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with EtOAc (50 mL)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec7ff57f55744f2cb91e51d518848389
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

Loading…