Tributylphosphine → HCID 86714757, compound

HRID 1055079Notes

Reaction equation

HRID 1055079 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-692270201edb47f2b8330de5732e8d22
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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