Tributylstannane → HCID 178462423, compound

HRID 1766888Notes

Reaction equation

HRID 1766888 reaction equation
C(OC([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][C@:14]([C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:44]=1[F:50])([CH2:37][N:38]1[CH:42]=[N:41][CH:40]=[N:39]1)[C@H:15]([S:17][C@@H:18]1[CH2:23][O:22][C@@H:21](/[CH:24]=[CH:25]/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][C:29]=2[F:36])[O:20][CH2:19]1)[CH3:16])=[O:12])=O)C=C.C([SnH](CCCC)CCCC)CCC.CCCCCC>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][C@:14]([C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:44]=1[F:50])([CH2:37][N:38]1[CH:42]=[N:41][CH:40]=[N:39]1)[C@H:15]([S:17][C@@H:18]1[CH2:23][O:22][C@@H:21](/[CH:24]=[CH:25]/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][C:29]=2[F:36])[O:20][CH2:19]1)[CH3:16])=[O:12]

Participants

6

Reactant 3

HCID 5948TributylstannaneHCID 8058HexaneHCID 178459923HCID 178459923, compound

Product 1

HCID 178462423HCID 178462423, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-Cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl 4-(allyloxycarbonyloxy)butyrate (352 mg, 4.94×10−4 mol) obtained from Example 11-(3) and bis(triphenylphosphine)dichloropalladium (2 mg) were dissolved in dichloromethane (3 ml). Tributyltin hydride (215 mg, 7.39×10−4 mol) was slowly added to the mixture at room temperature over a period of 5 minutes. After stirring at room temperature for 15 minutes further, hexane was added to the reaction mixture. The insoluble liberated oily material was separated by removing the supernatant liquid slowly. The insoluble residue was further washed twice with hexane. The oily residue was subjected to chromatography on a silica gel (15 g) column (eluent; ethyl acetate:hexane=3:1˜1:0) to afford the title compound (289 mg, 93% yield) as a colorless amorphous solid.

Workup

  1. customThe insoluble liberated oily material was separated
  2. customby removing the supernatant liquid slowly
  3. washThe insoluble residue was further washed twice with hexane

Sources & evidence

ORD record
ord-7113b5766bd94f63be6a10dcd4401d8c
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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