Carbon tetrabromide → HCID 71540230, compound

HRID 1516406Notes

Reaction equation

HRID 1516406 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]([CH3:33])(=[N:29][CH2:30][CH2:31]O)=[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:54]>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]([CH3:33])(=[N:29][CH2:30][CH2:31][Br:54])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 25270557HCID 25270557, compound

Product 1

HCID 71540230HCID 71540230, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-methyl-N-[2-hydroxy-ethyl]sulfoximide (0.6 g, 0.00118 mol) in DCM (6 mL) was added triphenyl phosphine (460 mg, 0.00177 mol) followed by carbon tetrabromide (589 mg, 0.00177 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, 10-50% ethyl acetate in hexane) gave 300 mg of titled product.

Workup

  1. customReaction mixture
  2. customSubsequent work up and column purification (100-200 mesh silica gel, 10-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-436e078bd22d4ea3969b7be2f371901a
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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