Potassium Carbonate → N-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethvl]-2,3-dihydro-5-(triisopropylsilyl)oxy-1H-isoindole difumarate

HRID 2184593Notes

Reaction equation

HRID 2184593 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.Br[C:21]1([CH3:40])[CH:26]=[CH:25][C:24]([O:27][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])=[CH:23][C:22]1(Br)[CH3:38].[C:41]([O-:44])([O-:43])=O.[K+].[K+]>C(#N)C>[C:4]([OH:27])(=[O:8])/[CH:5]=[CH:18]/[C:41]([OH:44])=[O:43].[C:24]([OH:27])(=[O:8])/[CH:25]=[CH:26]/[C:41]([OH:44])=[O:43].[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]4[CH2:38][C:22]5[C:21](=[CH:26][CH:25]=[C:24]([O:27][Si:28]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:35]([CH3:36])[CH3:37])[CH:23]=5)[CH2:40]4)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amineHCID 670710041,2-Dibromo-4-(triisopropyisilyl)oxy-xylene

Product 1

HCID 67071185N-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethvl]-2,3-dihydro-5-(triisopropylsilyl)oxy-1H-isoindole difumarate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (1.52 g, 5.73 mmol), 1,2-dibromo-4-(triisopropylsilyl)oxy-xylene (2.4 g, 5.7 mmol) and K2CO3 (1.8 g, 13 mmol) in acetonitrile (300 ml) was stirred overnight (18 hours) at room temperature. The mixture was filtered and the solvent was stripped. The residue was purified by flash chromatography over a silica gel column (7 gm of SiO2; eluted with 1-3% CH3OH in dichloromethane. The product was purified (weight: 900 mg) was converted to the fumarate salt by treatment with fumaric acid (194 mg) in hot ethanol. The crystals were collected and weighed 590 mg, m.p. 208°-210° C. ANALYSIS: Calculated for C31H44FN3O2Si.2C4H4O4: 60.84%C 6.81%H 5.46%N Found: 60.41%C 6.87%H 5.35%N

Workup

  1. filtrationThe mixture was filtered
  2. customThe residue was purified by flash chromatography over a silica gel column (7 gm of SiO2
  3. washeluted with 1-3% CH3OH in dichloromethane
  4. customThe product was purified (weight: 900 mg)
  5. customThe crystals were collected

Sources & evidence

ORD record
ord-87e9767a16164ea6afe94cc56ee0b16d
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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