Pyridine → HCID 59351604, compound

HRID 1889418Notes

Reaction equation

HRID 1889418 reaction equation
[CH2:1]([C:3]1[S:29][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][C:15]=3[F:28])[C:8](=[O:12])[NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[CH3:30][C:31]1([CH3:43])[CH2:35][C:34]2[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:33]=2[O:32]1.C(N(CC)CC)C.N1C=CC=CC=1>ClCCl.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:30][C:31]1([CH3:43])[CH2:35][C:34]2[CH:36]=[C:37]([N:9]3[C:10](=[O:11])[C:5]4[CH:4]=[C:3]([CH2:1][CH3:2])[S:29][C:6]=4[N:7]([CH2:13][C:14]4[CH:19]=[CH:18][C:17]([C:20]5[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=5)=[CH:16][C:15]=4[F:28])[C:8]3=[O:12])[CH:38]=[CH:39][C:33]=2[O:32]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 23005350(2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acidHCID 593515684'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3'-fluorobiphenyl-2-carbonitrile

Product 1

HCID 59351604HCID 59351604, compoundYield 79.4%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension (20 mL) of 4′-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3′-fluorobiphenyl-2-carbonitrile (0.5 g), (2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acid (0.47 g), triethylamine (0.86 mL), pyridine (0.48 mL) and molecular sieves 4A (1 g) in dichloromethane was added copper(II) acetate (0.45 g) and the mixture was stirred for 2 days. The reaction mixture was diluted with ethyl acetate, insoluble material was filtered off through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow solid (0.54 g, 79%).

Workup

  1. filtrationwas filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f4645a1c339435c97eec53484eb159d
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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