Dimethylformamide → (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-4-bromo-3-methylthiophene-2-carboxamide

HRID 1821441Notes

Reaction equation

HRID 1821441 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.S(Cl)(Cl)=O.CN(C=O)C.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH2:37])=[N:21]1.C(N(CC)CC)C>C1COCC1.ClCCl>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH:37][C:7]([C:4]2[S:5][CH:6]=[C:2]([Br:1])[C:3]=2[CH3:10])=[O:9])=[N:21]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27570734-Bromo-3-methylthiophenecarboxylic acidHCID 69001756HCID 69001756, compound

Product 1

HCID 69000757(E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-4-bromo-3-methylthiophene-2-carboxamideYield 24%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Example 29, 4-bromo-3-methylthiophene-2-carboxylic acid (0.10 g, 0.47 mmol) was treated with thionyl chloride (53 μL, 0.72 mmol), DMF (5.0 μL, 0.085 mmol) and dichloromethane (2.0 mL), followed by reacting with Compound 2 (0.10 g, 0.43 mmol), triethylamine (60 μL, 1.1 mmol) and THF (2.0 mL) to obtain Compound 353 (44 mg, 24%).

Sources & evidence

ORD record
ord-2c8d633f6184483fa57eca6d9b8c860c
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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