3-(2-Bromo-3-pyridyl)isoxazole → 2-Chloro-4,4-difluoro-1'-[[1-(3-isoxazol-3-yl-2-pyridyl)-3-methyl-pyrazol-4-yl]methyl]spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]

HRID 1517610Notes

Reaction equation

HRID 1517610 reaction equation
[Cl:1][C:2]1[S:6][C:5]2[C:7]3([O:20][CH2:21][C:22]([F:24])([F:23])[C:4]=2[CH:3]=1)[CH2:12][CH2:11][N:10]([CH2:13][C:14]1[C:15]([CH3:19])=[N:16][NH:17][CH:18]=1)[CH2:9][CH2:8]3.Br[C:26]1[C:31]([C:32]2[CH:36]=[CH:35][O:34][N:33]=2)=[CH:30][CH:29]=[CH:28][N:27]=1>>[Cl:1][C:2]1[S:6][C:5]2[C:7]3([O:20][CH2:21][C:22]([F:23])([F:24])[C:4]=2[CH:3]=1)[CH2:12][CH2:11][N:10]([CH2:13][C:14]1[C:15]([CH3:19])=[N:16][N:17]([C:26]2[C:31]([C:32]4[CH:36]=[CH:35][O:34][N:33]=4)=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:18]=1)[CH2:9][CH2:8]3

Participants

3

Reactant 2

HCID 582685393-(2-Bromo-3-pyridyl)isoxazoleHCID 178434546HCID 178434546, compound

Product 1

HCID 582686132-Chloro-4,4-difluoro-1'-[[1-(3-isoxazol-3-yl-2-pyridyl)-3-methyl-pyrazol-4-yl]methyl]spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]Yield 45%

Procedure

This compound is essentially prepared as described in Example 36 by using 2-chloro-4,4-difluoro-1′-[(3-methyl-1H-pyrazol-4-yl)methyl]spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine] and 3-(2-bromo-pyrid-3-yl)isoxazole as starting material. Residue is purified by normal phase Isco chromatography (ethyl acetate is used as eluent) to yield 45% of the title compound: mass spectrum (m/z): 518 (M+1)

Workup

  1. customThis compound is essentially prepared
  2. customResidue is purified by normal phase Isco chromatography (ethyl acetate is used as eluent)

Sources & evidence

ORD record
ord-ad3dd8ccef8c429998edae1838cb6de3
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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