Water → HCID 22249918, compound

HRID 966033Notes

Reaction equation

HRID 966033 reaction equation
Br[C:2]1[C:3]([CH3:20])=[N:4][N:5]2[C:10]3[N:11]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:12][CH2:13][C:9]=3[C:8]([CH3:19])=[N:7][C:6]=12.[O:21]1[C:25]([Sn](CCCC)(CCCC)CCCC)=[CH:24][C:23]2[CH:39]=[CH:40][CH:41]=[CH:42][C:22]1=2.C(OCC)(=O)C.O>CN(C)C=O.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>[O:21]1[C:25]([C:2]2[C:3]([CH3:20])=[N:4][N:5]3[C:10]4[N:11]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:12][CH2:13][C:9]=4[C:8]([CH3:19])=[N:7][C:6]=23)=[CH:24][C:23]2[CH:39]=[CH:40][CH:41]=[CH:42][C:22]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 38258561-benzofuran-2-yl(tributyl)stannaneHCID 22249888HCID 22249888, compound

Product 1

HCID 22249918HCID 22249918, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-8-(1-ethylpropyl)-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (300 mg, 0.89 mmol), benzo[b]furan-2-yl(tributyl)tin (0.72 g, 1.78 mmol) and Pd(PPh3)4 (103 mg, 0.90 mmol) in N,N-dimethylformamide (15 mL) was stirred at 120° C. for one day. Ethyl acetate and water were added thereto, followed by filtering through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane), to give the title compound (111 mg) as white crystals.

Workup

  1. filtrationby filtering through Celite
  2. washThe organic layer of the filtrate was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3b3ff42cd4eb40a1a054f9224aa78be8
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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