Dimethylformamide → HCID 67266527, compound

HRID 2428071Notes

Reaction equation

HRID 2428071 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[C:14]([S:16][C:17]3[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[C:19]([CH3:28])[CH:18]=3)[CH:13]=[C:12]([C:29]#[C:30][C:31]3[CH:36]=[CH:35][C:34](Cl)=[CH:33][CH:32]=3)[N:11]=2)=[CH:4][CH:3]=1.[I-].C(C1C=CC([CH2:45][OH:46])=CC=1)#C.[CH2:49](N(CC)CC)C.CN([CH:59]=[O:60])C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:49][O:25][C:23](=[O:24])[CH2:22][O:21][C:20]1[CH:26]=[CH:27][C:17]([S:16][C:14]2[CH:15]=[C:10]([C:9]#[C:8][C:5]3[CH:6]=[CH:7][C:2]([CH2:59][OH:60])=[CH:3][CH:4]=3)[N:11]=[C:12]([C:29]#[C:30][C:31]3[CH:36]=[CH:35][C:34]([CH2:45][OH:46])=[CH:33][CH:32]=3)[CH:13]=2)=[CH:18][C:19]=1[CH3:28]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 30165Iodide IonHCID 11170993(4-Ethynylphenyl)methanolHCID 57826288HCID 57826288, compound

Product 1

HCID 67266527HCID 67266527, compound

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

7-(2,6-Dibromo-pyridin-4-ylsulfanyl)-2-methyl-phenoxy}-acetic acid methyl ester (0.3 g; 0.67 mmol, prepared as described in example 6), cupper iodide (3.8 mg; 0.02 mmol), 4-ethynylbenzylalcohol (266 mg; 2.01 mmol) and bis(triphenylphosphine) palladium (II) chloride (18.8 mg; 0.027 mmol) were added to a dry reaction flask under an atmosphere of nitrogen. Triethylamine (2 ml) and DMF (2 ml) was added and the reaction mixture was reacted at 70° C. for 10 min in a microwave oven. The reaction mixture was purified by preparative HPLC (method B) to give {4-[2,6-bis-(4-hydroxymethyl-phenylethynyl)-pyridin-4-ylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester. Yield: 260 mg; 70%.

Workup

  1. additionwere added to a dry reaction flask under an atmosphere of nitrogen
  2. customthe reaction mixture was reacted at 70° C. for 10 min in a microwave oven
  3. customThe reaction mixture was purified by preparative HPLC (method B)

Sources & evidence

ORD record
ord-e25d93e5c67344b9baa7ce4804400122
Source dataset
uspto-grants-2011_06
Patent number
US07968723B2

Reaction notes

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