Ethyl Acetate → 4-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclo pentyl]oxy}-N-[(1S)-5-chloro-3,3-dimethyl-2,3-di hydro-1H-inden-1-yl]pyridin-2-amine

HRID 447660Notes

Reaction equation

HRID 447660 reaction equation
CC(C)([O-])C.[K+].[Si:7]([O:14][C@@H:15]1[C@H:19]([CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:18][C@@H:17]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32](Cl)[CH:31]=2)[CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[Cl:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[C@@H:43]([NH2:47])[CH2:42][C:41]2([CH3:49])[CH3:48].CCOC(C)=O>COCCOC>[Si:22]([O:21][C@@H:20]1[C@H:19]([CH2:15][O:14][Si:7]([C:10]([CH3:12])([CH3:11])[CH3:13])([CH3:9])[CH3:8])[CH2:18][C@@H:17]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]([NH:47][C@@H:43]3[C:44]4[C:40](=[CH:39][C:38]([Cl:37])=[CH:46][CH:45]=4)[C:41]([CH3:49])([CH3:48])[CH2:42]3)[CH:31]=2)[CH2:16]1)([C:25]([CH3:27])([CH3:28])[CH3:26])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 57572828(1S)-5-chloro-3,3-dimethylindan-1-amineHCID 866187294-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]oxy}-2-chloropyridine

Product 1

HCID 667982064-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclo pentyl]oxy}-N-[(1S)-5-chloro-3,3-dimethyl-2,3-di hydro-1H-inden-1-yl]pyridin-2-amineYield 18%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a mixture of [1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-yl](chloro)[(2,3-η)-(1Z)-1-phenylprop-1-ene-2,3-diyl]palladium(2+) (3.4 mg, 0.0000052 mol) and potassium tert-butoxide (32.0 mg, 0.000286 mol) under an atmosphere of argon was added 4-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-cyclopentyl]oxy}-2-chloropyridine (0.1226 g, 0.0002596 mol) in 1.00 ml DME, followed by (1S)-5-chloro-3,3-dimethylindan-1-amine (0.048 g, 0.00025 mol) in 1 ml DME. The mixture was stirred overnight, and the solution was poured into 50 ml EtOAc, washed with 10 ml water and concentrated. The residue was purified by preparative plate chromatography (70% EtOAc/hexanes) to afford the title compound (28.0 mg, 18.0%).

Workup

  1. washwashed with 10 ml water
  2. concentrationconcentrated
  3. customThe residue was purified by preparative plate chromatography (70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cce4c5b9a4334288b3cb9e57d6ee9ad7
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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