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2-Chloro-6-(tributylstannyl)pyrazine → 3-(6-chloropyrazin-2-yl)-5-(2,6-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1529283
Notes
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Reaction equation

HRID 1529283 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[N:13]=[C:12]2I.[Cl:25][C:26]1[CH:31]=[N:30][CH:29]=[C:28]([Sn](CCCC)(CCCC)CCCC)[N:27]=1>CN(C=O)C.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Cl:25][C:26]1[N:27]=[C:28]([C:12]2[C:11]3[C:15](=[CH:16][CH:17]=[C:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[CH:10]=3)[N:14]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[N:13]=2)[CH:29]=[N:30][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 117740572-Chloro-6-(tributylstannyl)pyrazineHCID 679597535-(2,6-difluoro-phenyl)-3-iodo-1-(tetrahydro-pyran-2-yl)-1H-indazole

Product 1

HCID 867097633-(6-chloropyrazin-2-yl)-5-(2,6-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleYield 98%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
105 °C

Procedure

A glass microwave reaction vessel was charged with 5-(2,6-difluorophenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 14 (1.00 g, 2.272 mmol) and 2-chloro-6-(tributylstannyl)pyrazine 1b (1.375 g, 3.41 mmol) in DMF (9 mL) followed by Pd(PPh3)4 (0.131 g, 0.114 mmol) and CuI (7.70 μL, 0.227 mmol). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 105° C. for 1 h. The resulting mixture was diluted with DCM. The organic layer was separated, washed with water, dried, filtered and concentrated. The residue was purified by silica gel chromatography (eluting with 0-15% EtOAc in Hexanes) to give 3-(6-chloropyrazin-2-yl)-5-(2,6-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.95 g, 2.22 mmol, 98% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 427.0 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. customThe organic layer was separated
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (eluting with 0-15% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-909bc356e6084b1b923649a49c73a2b9
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090593B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes