Diisopropylamine → 5-(4-Butoxyphenylethynyl)furan-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

HRID 2426679Notes

Reaction equation

HRID 2426679 reaction equation
[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[O:18][C:19](Br)=[CH:20][CH:21]=3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1.[CH2:24]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[CH:36])=[CH:31][CH:30]=1)[CH2:25][CH2:26][CH3:27].C(NC(C)C)(C)C>CN(C)C=O.O1CCCC1.[Cu]I>[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[O:18][C:19]([C:36]#[C:35][C:32]4[CH:33]=[CH:34][C:29]([O:28][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:30][CH:31]=4)=[CH:20][CH:21]=3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 27751201-Butoxy-4-ethynylbenzeneHCID 671477595-Bromofuran-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 588665915-(4-Butoxyphenylethynyl)furan-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromofuran-2-carboxylic acid [4-(3-dimethylaminopyrrolid in-1-yl)phenyl]amide (75 mg) was dissolved together with 1-butoxy-4-ethynylbenzene (35 mg) in N,N-dimethylformamide (1 ml) and, under argon, added dropwise to a suspension of Pd(tBu3P)2Cl2 (4 mg), copper (I) iodide (75 mg) and N,N-diisopropylamine (20 mg) in anhydrous tetrahydrofuran (3 ml). The mixture was stirred at room temperature for 8 hours. The reaction was worked up by filtration through a syringe filter and concentrated, and the crude product was purified by preparative HPLC. This resulted in the product with the molecular weight of 471.6 (C29H33N3O3); MS (ESI): 472 (M+H+) as hydrotrifluoroacetate.

Workup

  1. filtrationThe reaction was worked up by filtration through a syringe
  2. filtrationfilter
  3. concentrationconcentrated
  4. customthe crude product was purified by preparative HPLC
  5. customThis resulted in the product with the molecular weight of 471.6 (C29H33N3O3)

Sources & evidence

ORD record
ord-0a34dc2f0ebb49d4a00f45805b3b19e0
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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