2-Bromonicotinaldehyde → 2-[4-[(2-Fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)methyl]-3-methyl-pyrazol-1-yl]pyridine-3-carbaldehyde

HRID 1517561Notes

Reaction equation

HRID 1517561 reaction equation
Br[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:10][C:11]1[S:15][C:14]2[C:16]3([O:29][CH2:30][CH2:31][C:13]=2[CH:12]=1)[CH2:21][CH2:20][N:19]([CH2:22][C:23]1[C:24]([CH3:28])=[N:25][NH:26][CH:27]=1)[CH2:18][CH2:17]3>>[F:10][C:11]1[S:15][C:14]2[C:16]3([O:29][CH2:30][CH2:31][C:13]=2[CH:12]=1)[CH2:21][CH2:20][N:19]([CH2:22][C:23]1[C:24]([CH3:28])=[N:25][N:26]([C:2]2[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:27]=1)[CH2:18][CH2:17]3

Participants

3

Reactant 2

HCID 47149512-BromonicotinaldehydeHCID 178434545HCID 178434545, compound

Product 1

HCID 582686272-[4-[(2-Fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)methyl]-3-methyl-pyrazol-1-yl]pyridine-3-carbaldehydeYield 83%

Procedure

The compound of Preparation 13 is essentially prepared as described in Preparation 12 by using 2-bromopyridine-3-carbaldehyde and 2-fluoro-1′-[(3-methyl-1H-pyrazol-4-yl)methyl]spiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine]. Residue is purified by normal phase Isco chromatography to yield 83% of the title compound. MS (m/z): 427 (M+1).

Workup

  1. customThe compound of Preparation 13
  2. customis essentially prepared
  3. customas described in Preparation 12
  4. customResidue is purified by normal phase Isco chromatography

Sources & evidence

ORD record
ord-c1ebbe08e94244fb975195e1a59fc788
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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