Pyridine → HCID 131722541, compound

HRID 1976478Notes

Reaction equation

HRID 1976478 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.C[C:27]1([C:51]([NH2:53])=[O:52])[C:32]([CH3:34])([CH3:33])[S:31][CH2:30][CH2:29][N:28]1[S:35]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]#[C:47][CH2:48][CH2:49]O)=[CH:40][CH:39]=1)(=[O:37])=[O:36].C(Br)(Br)(Br)[Br:55]>C1COCC1>[Br:55][CH2:49][CH2:48][C:47]#[C:46][CH2:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([S:35]([N:28]2[CH2:29][CH2:30][S:31][C:32]([CH3:34])([CH3:33])[CH:27]2[C:51]([NH2:53])=[O:52])(=[O:36])=[O:37])=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86587133HCID 86587133, compound

Product 1

HCID 131722541HCID 131722541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.123 g (8.093 mmol) of triphenylphosphine and 0.373 mL (4.61 mmol) of pyridine in 40 mL of dry THF under nitrogen was added 1.73 g (4.046 mmol) of methyl 4-({4-[(5-hydroxy-2-pentynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholine carboxamide. The solution was cooled in a water bath and 1.34 g (4.046 mmol) of carbon tetrabromide was added and the resulting mixture was stirred for 3h. The resulting suspension was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate:hexanes (1:8) to provide 1.726 g (87%) of methyl 4-({4-[(5-bromo-2-pentynyl)oxy]phenyl}sulfonyl-2,2-dimethyl-3-thiomorpholine carboxamide as a pale yellow oil. Electrospray Mass Spec: 492.0 (M+H)+

Workup

  1. temperatureThe solution was cooled in a water bath
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with ethyl acetate:hexanes (1:8)

Sources & evidence

ORD record
ord-99c6a62da2184e0caeae12fa696be20d
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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