Dibutyltin dichloride → HCID 59314171, compound

HRID 1047944Notes

Reaction equation

HRID 1047944 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH2:15])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[O:16]1[C:20]2[C:21]([CH:25]=O)=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17]1.C1([SiH3])C=CC=CC=1.C([Sn](Cl)(Cl)CCCC)CCC>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1([NH:15][CH2:25][C:21]2[C:20]3[O:16][CH2:17][CH2:18][C:19]=3[CH:24]=[CH:23][CH:22]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehydeHCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 59314171HCID 59314171, compoundYield 190.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 10 mL microwave reaction vessel is charged with 2-amino-indan-2-carboxylic acid ethyl ester (500 mg, 2.44 mmol) and dry tetrahydrofuran (THF, 5 mL). A stirring bar is added and stirring is initiated. After dissolution, 2,3-dihydro-1-benzofuran-7-carbaldehyde (361 mg, 2.43 mmol) is added. Stirring is continued. Phenylsilane ([694-18-1], 0.61 mL, 4.87 mmol) and dibutyltin dichloride (53 μL, 244 μM) are added. The reaction vial is crimped sealed and placed in a Smith Microwave Apparatus. The pre-stir time is set to 10 sec. Heating is set at 100° C. for 10 min. The contents of the reaction vial are transferred to a round bottom flask and evaporated by pumping to a constant weight yields 1.56 g of light yellow oil. This material is dissolved in DCM (10 mL) and applied to an ISCO Companion that is fitted with a 40 g Cartridge (silica). The column is eluted with 5% EtOAc/heptanes for 3 column volumes followed by a linear gradient to 50% EtOAc/heptanes over 10 column volumes and then 90% EtOAc/heptanes for 2 column volumes. 14 mL fractions of UV active eluent are collected. Fractions 7 to 11 are combined and evaporated by pumping to constant weight yields 0.59 g of white solid material (0.52 g, 63%).

Workup

  1. additionA stirring bar is added
  2. additionis added
  3. stirringStirring
  4. customThe reaction
  5. customvial is crimped sealed
  6. temperatureHeating
  7. waitis set at 100° C. for 10 min
  8. customThe contents of the reaction
  9. customvial are transferred to a round bottom flask
  10. customevaporated

Sources & evidence

ORD record
ord-434964a238d7434fbfe3124af26e9c16
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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