Diisopropylamine → 5-p-Tolylethinylfuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

HRID 2426657Notes

Reaction equation

HRID 2426657 reaction equation
C(NC(C)C)(C)C.[CH3:8][N:9]([CH3:30])[CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[O:25][C:26](Br)=[CH:27][CH:28]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:11]1.[C:31]([C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)#[CH:32]>CN(C=O)C>[CH3:8][N:9]([CH3:30])[CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[O:25][C:26]([C:32]#[C:31][C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)=[CH:27][CH:28]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 13018p-EthynyltolueneHCID 671477595-Bromofuran-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 588675915-p-Tolylethinylfuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.042 ml of diisopropylamine was added under argon to 3.8 mg of Pd(tBu)2Cl2 and 0.95 mg of Cul in 0.2 ml of DMF. A solution of 94.6 mg of 5-bromofuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]-amide in 0.3 ml of DMF and a solution of 4-ethynyltoluene in 0.3 ml of DMF were then added dropwise. The solution was stirred at room temperature overnight. The precipitate which had separated out was filtered off with suction and the filtrate purified by preparative HPLC. The desired product with the molecular weight of 413.52; MS (ESI): 414 was obtained as hydrotrifluoroacetate.

Workup

  1. customThe precipitate which had separated out
  2. filtrationwas filtered off with suction
  3. customthe filtrate purified by preparative HPLC
  4. customMS (ESI): 414 was obtained as hydrotrifluoroacetate

Sources & evidence

ORD record
ord-ad2e8fe8664b4aa79273a91d310000ed
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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