Carbon tetrabromide → HCID 57657974, compound

HRID 607450Notes

Reaction equation

HRID 607450 reaction equation
O[CH2:2][CH2:3][CH2:4][S:5](=[O:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[N:6][C:7](=[O:31])[C:8]1[CH:13]=[C:12]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([C:25]3[O:26][CH:27]=[CH:28][C:29]=3[CH3:30])=[O:24])[CH:17]=2)[CH:11]=[N:10][CH:9]=1.C(Br)(Br)(Br)[Br:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:40][CH2:2][CH2:3][CH2:4][S@:5](=[O:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[N:6][C:7](=[O:31])[C:8]1[CH:13]=[C:12]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([C:25]3[O:26][CH:27]=[CH:28][C:29]=3[CH3:30])=[O:24])[CH:17]=2)[CH:11]=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57657830HCID 57657830, compound

Product 1

HCID 57657974HCID 57657974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

N-[(3-hydroxypropyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide (1.71 g, 3.24 mmol) was dissolved in anhydrous CH2Cl2 (5 mL) and the resulting solution was cooled to 0° C. A solution of carbon tetrabromide (1.565 g ) in CH2Cl2 (3 mL) was added dropwise followed by a dropwise addition of a solution of triphenylphosphine (1.24 g) in CH2Cl2 (3 mL). The reaction was stirred at room temperature for 1.5 hours and then partitioned between saturated aqueous NaHCO3 and dichloromethane. The organic layer was separated, washed with brine (1×), dried with anhydrous Na2SO4, and concentrated with silica gel under reduced pressure. A gradient column chromatography (acetone-hex: from 1:10 to 1:4) rendered title compound as white solid in amount of 1.56 g (82%).

Workup

  1. custompartitioned between saturated aqueous NaHCO3 and dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine (1×)
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated with silica gel under reduced pressure

Sources & evidence

ORD record
ord-2e8a5de0e4f54afa9444b31c7931589f
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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