Dibutyltin dichloride → t-Butyl (2-{4-[3-(3-cyclopentyloxy-4-methoxy-phenylamino)-propenyl]-benzoylamino}-phenyl)-carbamate

HRID 1180808Notes

Reaction equation

HRID 1180808 reaction equation
O=[CH:2][CH:3]=[CH:4][C:5]1[CH:27]=[CH:26][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:10])=[CH:7][CH:6]=1.[CH:28]1([O:33][C:34]2[CH:35]=[C:36]([CH:38]=[CH:39][C:40]=2[O:41][CH3:42])[NH2:37])[CH2:32][CH2:31][CH2:30][CH2:29]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH:28]1([O:33][C:34]2[CH:35]=[C:36]([NH:37][CH2:2][CH:3]=[CH:4][C:5]3[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:10])=[CH:26][CH:27]=3)[CH:38]=[CH:39][C:40]=2[O:41][CH3:42])[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 27793343-(Cyclopentyloxy)-4-methoxyanilineHCID 72479807t-Butyl {2-[4-(3-oxo-propenyl)-benzoylamino]-phenyl}-carbamate

Product 1

HCID 86602773t-Butyl (2-{4-[3-(3-cyclopentyloxy-4-methoxy-phenylamino)-propenyl]-benzoylamino}-phenyl)-carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution at room temperature of compound XVI (210 mg, 0.57 mmol), 3-cyclopentyloxy-4-methoxy-aniline (125 mg, 0.60 mmol) or ArNH2 (1.05–1.2 equiv.) in anhydrous THF (7 ml) under nitrogen were added dibutyltin dichloride (3.5 mg, 0.01 mmol). After 10 min, phenylsilane (78 μl, 0.63 mmol) was added dropwise. After 3 days, the reaction mixture was concentrated and directly purified by flash chromatography on silica gel (AcOEt/hexane:30/70→50/50) to afford the title compound XVIIa as a yellow sticky oil.

Workup

  1. waitAfter 3 days
  2. concentrationthe reaction mixture was concentrated
  3. customdirectly purified by flash chromatography on silica gel (AcOEt/hexane:30/70→50/50)

Sources & evidence

ORD record
ord-b2f4b4a1cf3942319fc9bd1aa4836022
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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