Carbon tetrabromide → N-{[4-(Bromomethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

HRID 607428Notes

Reaction equation

HRID 607428 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:37])(=[O:36])=[N:10][C:11](=[O:35])[C:12]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]4[O:30][CH:31]=[CH:32][C:33]=4[CH3:34])=[O:28])[CH:21]=3)[CH:15]=[N:14][CH:13]=2)=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:39].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:39][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:37])(=[O:36])=[N:10][C:11](=[O:35])[C:12]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]4[O:30][CH:31]=[CH:32][C:33]=4[CH3:34])=[O:28])[CH:21]=3)[CH:15]=[N:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57657893N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

Product 1

HCID 57657978N-{[4-(Bromomethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide (0.1 g, 0.195 mmol) and CBr4 (0.097 g, 0.293 mmol) were dissolved in CH2Cl2 (0.485 mL) and the resulting solution was cooled to 0° C. PPh3 (0.858 g, 0.293 mmol) was dissolved in CH2Cl2 (0.250 mL) and then added dropwise to the 0° C. reaction mixture. Subsequently the reaction was allowed to warm to room temperature and stir for ˜1.5 h. The reaction was then diluted with CH2Cl2 (5 mL) and the resulting organic mixture was washed with a saturated aqueous solution of NaHCO3 (5 mL), then with brine (5 mL). The organic layer was dried anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude product was then taken on without further purification.

Workup

  1. additionadded dropwise to the 0° C. reaction mixture
  2. temperatureto warm to room temperature
  3. washthe resulting organic mixture was washed with a saturated aqueous solution of NaHCO3 (5 mL)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was then taken on without further purification

Sources & evidence

ORD record
ord-bd34cbaa7ac5417a9407a81dba5797e8
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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