Tributylstannane → HCID 57948925, compound

HRID 1992285Notes

Reaction equation

HRID 1992285 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:27])[CH2:14][C:13]([CH2:16]I)([CH3:15])[S:12][C:11]([NH:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C([SnH](CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:27])[CH2:14][C:13]([CH3:16])([CH3:15])[S:12][C:11]([NH:18][C:19](=[O:26])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 8857Ethyl AcetateHCID 57948943HCID 57948943, compound

Product 1

HCID 57948925HCID 57948925, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-((4S)-4-(3-bromo-4-fluorophenyl)-6-(iodomethyl)-4,6-dimethyl-5,6-dihydro-4H-1,3-thiazin-2-yl)benzamide (0.13 g, 0.23 mmoles, 1.0 equiv) in toluene (1.5 mL) is added 2-2′-azo-bis-isobutyronitrile (0.006 g, 0.03 mmoles, 0.15 equiv) and tri-n-butyltin hydride. The reaction mixture is stirred at room temperature for 3 h and concentrated under reduced pressure. The solvent is removed under reduced pressure and the residue is purified by silica gel chromatography eluting with a linear gradient of 5% ethyl acetate:hexanes to 20% ethyl acetate:hexanes to give the title compound (25% yield): MS (m/z): 435, 437 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is purified by silica gel chromatography
  4. washeluting with a linear gradient of 5% ethyl acetate

Sources & evidence

ORD record
ord-8b59f3aeee0344898b31091e7dc53bbd
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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