Ethyl Acetate → HCID 69002322, compound

HRID 1821389Notes

Reaction equation

HRID 1821389 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:18]=[CH:19]/[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][N:21]=2)=[C:7]([NH:9][C:10]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:11])[CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:49].C(OCC)(=O)C>CN(C=O)C>[NH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](/[CH:19]=[CH:18]/[C:6]2[CH:5]=[CH:4][C:3]([CH2:2][Br:49])=[CH:8][C:7]=2[NH:9][C:10]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:11])=[N:21]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66585324HCID 66585324, compound

Product 1

HCID 69002322HCID 69002322, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 108 (0.30 g, 0.77 mmol) was dissolved in DMF (12 mL) and the solution was added with triphenylphosphine (0.45 g, 1.5 mmol) and carbon tetrabromide (0.51 g, 1.5 mmol), followed by stirring at room temperature for 1 hour. After the reaction, the mixture was added with ethyl acetate and washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was concentrated under reduced pressure to obtain (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]-5-(bromomethyl)phenyl}-3-methylthiophene-2-carboxamide.

Workup

  1. customAfter the reaction
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7f8b006403a441d9ae5603469baa55a5
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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