Carbon tetrabromide → HCID 86652066, compound

HRID 1516415Notes

Reaction equation

HRID 1516415 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH2:33][CH2:34]O)(=[N:29][C:30](=[O:32])[CH3:31])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:56]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH2:33][CH2:34][Br:56])(=[N:29][C:30](=[O:32])[CH3:31])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86652065HCID 86652065, compound

Product 1

HCID 86652066HCID 86652066, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-(2-hydroxy ethyl)-N-acetyl sulfoximide (90 mg, 0.000168 mol) in DCM (15 mL) was added triphenyl phosphine (44 mg, 0.000168 mol) with stirring followed by carbon tetrabromide (55 mg, 0.000168 mol) at 25-30° C. Reaction mixture was stirred at same temperature for 3 hr. Subsequent work up and column purification (100-200 mesh silica gel, 50% ethyl acetate in hexane) gave 50 mg of titled product in 50% yield.

Workup

  1. customReaction mixture
  2. stirringwas stirred at same temperature for 3 hr
  3. customSubsequent work up and column purification (100-200 mesh silica gel, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3795c47f39b14950b03fb64e2d2abf8a
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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