Hexamethylditin → 1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol

HRID 216368Notes

Reaction equation

HRID 216368 reaction equation
Br[C:2]1[S:6][N:5]=[CH:4][CH:3]=1.Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:46])([CH3:45])[CH2:15][C:16]2[N:17]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:18]=[C:19]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[N:20]=2)=[CH:10][CH:9]=1.C[Sn](C)C.C[Sn](C)C>O1CCOCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:19]1[N:20]=[C:16]([CH2:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:2]3[S:6][N:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)([OH:46])[CH3:45])[N:17]([C:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:18]=1

Participants

7

Reactant 3

HCID 6327618HexamethylditinHCID 126311745-Bromo-1,2-thiazoleHCID 591619942-(4-bromophenyl)-1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]propan-2-ol

Product 1

HCID 686677351-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Palladium tetrakis(triphenylphosphine) (39 mg, 0.03 mmol) was added to a degassed, ambient temperature solution of 5-bromoisothiazole (55 mg, 0.34 mmol), 2-(4-bromophenyl)-1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]propan-2-ol (200 mg, 0.34 mmol) and hexamethylditin (110 mg, 0.34 mmol) in 1,4-dioxane (15 mL). After stirring at 90° C. for 16 h, the reaction mixture was diluted with water and extracted with ethyl acetate and methylene chloride. The combined organic extracts were concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol.

Workup

  1. extractionextracted with ethyl acetate and methylene chloride
  2. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-237fa4327f57447ba8d9f978e23a8761
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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