Tris(propan-2-yl)silanethiol → HCID 66580466, compound

HRID 1528861Notes

Reaction equation

HRID 1528861 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27]Br)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH:29]([Si:32]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[SH:33])([CH3:31])[CH3:30]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][S:33][Si:32]([CH:34]([CH3:36])[CH3:35])([CH:37]([CH3:39])[CH3:38])[CH:29]([CH3:30])[CH3:31])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 3435097Tris(propan-2-yl)silanethiolHCID 665771991-[4'-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 66580466HCID 66580466, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[4′-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (1.0 g, 2.27 mmol) and triisopropylsilanethiol (0.488 mL, 2.27 mmol) were dissolved in DMF (25 mL) and the solution was degassed with N2 for 10 minutes. Cesium carbonate was added and the reaction stirred overnight under N2 atmosphere. Standard aqueous workup afforded a mixture of the desired product plus de-protected free thiol which was taken directly to the next step.

Workup

  1. customthe solution was degassed with N2 for 10 minutes
  2. additionCesium carbonate was added
  3. customStandard aqueous workup afforded

Sources & evidence

ORD record
ord-44840b9f3e004982bb039456bc8f178f
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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