Tributylphosphine → HCID 86714757, compound

HRID 2171874Notes

Reaction equation

HRID 2171874 reaction equation
[F:1][C:2]1[C:3]([NH:28][CH:29]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:30][CH2:31]O)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)=[N:6][CH:7]=1.[N+:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[Se:46]C#N)([O-:39])=[O:38].C(P(CCCC)CCCC)CCC>C1COCC1>[CH3:36][C:33]([CH3:34])([CH3:35])[CH:29]([NH:28][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)[N:4]=1)[CH2:30][CH2:31][Se:46][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[N+:37]([O-:39])=[O:38]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 1039312-Nitrophenyl selenocyanateHCID 71247355HCID 71247355, compound2×

Product 1

HCID 86714757HCID 86714757, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic 3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]-4,4-dimethyl-pentan-1-ol, 82a, (1.093 g, 2.120 mmol) and (2-nitrophenyl) selenocyanate (0.722 g, 3.180 mmol) in THF (8 mL) was added tributylphosphane (0.792 mL, 3.180 mmol). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The crude residue was purified by silica gel (0 to 100% EtOAc/Hexanes gradient) to afford 1.20 g of the desired product.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude residue was purified by silica gel (0 to 100% EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-c30cb7f7640a439088d23bd5ed014eb2
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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