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Acetonitrile → N-[6-(1-benzofuran-5-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

HRID 244739
Notes
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Reaction equation

HRID 244739 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[C:11]3[C:15]([CH:16]=[C:17](B4OC(C)(C)CC(C)(C)O4)[CH:18]=2)=[N:14][N:13](C2CCCCO2)[CH:12]=3)=[O:8])[N:6]=1.Br[C:36]1[CH:37]=[CH:38][C:39]2[O:43][CH:42]=[CH:41][C:40]=2[CH:44]=1.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].CC#N>O1CCOCC1.O.Cl[Pd]C1C=CC=CC=1C1C=CC=CC=1N(C)C.[C@H]12C[C@H](CC1)CC2PC1C[C@H]2C[C@@H]1CC2>[O:43]1[C:39]2[CH:38]=[CH:37][C:36]([C:17]3[CH:16]=[C:15]4[C:11]([CH:12]=[N:13][NH:14]4)=[C:10]([NH:9][C:7]([C:5]4[N:6]=[C:2]([CH3:1])[S:3][CH:4]=4)=[O:8])[CH:18]=3)=[CH:44][C:40]=2[CH:41]=[CH:42]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 61695Pentapotassium TriphosphateHCID 90015Benzofuran, 5-bromo-HCID 582558332-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide

Product 1

HCID 58356419N-[6-(1-benzofuran-5-yl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide
Yield 10.7%

Reagents, catalysts & solvents 3

HCID 178420574HCID 178420574, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

2-methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide (53 mg, 0.11 mmol) was dissolved in 1,4-Dioxane (0.4 mL) and added to 5-bromo-1-benzofuran (20 mg, 0.1 mmol, available from ABCR) in a microwave vessel. 1,4-Dioxane (0.4 ml) was added followed by chloro[2′-(dimethylamino)-2-biphenylyl]palladium-(1R,4S)-bicyclo[2.2.1]hept-2-yl[(1S,4R)-bicyclo[2.2.1]hept-2-yl]phosphane (1:1) (Solvias catalyst, 2 mg, 0.004 mmol, (heaped microspatula) available from ABCR) and a solution of potassium triphosphate (0.2 g, 0.1 mmol) in water (0.2 ml). The vessel was sealed and heated in CEM Discover using initial 150 W to 110° C. for 20 min. After cooling the solution was loaded onto a C18 SPE cartridge (pre-conditioned with MeCN/0.1% TFA) and flushed through with a further 3 ml MeCN/0.1% TFA. Solvent was removed by blowdown under a stream of nitrogen. The residue was dissolved in MeOH (0.51) and loaded onto a SCX-2 SPE cartridge (1 g) pre-conditioned with MeOH. The material was left on the column for 1 hr then eluted with 2M ammonia/MeOH and evaporated to dryness. The sample was purified by Mass Directed AutoPrep (Method C) to afford the title compound (4 mg).

Workup

  1. customThe vessel was sealed
  2. temperatureheated in CEM Discover
  3. customfor 20 min
  4. temperatureAfter cooling the solution
  5. customflushed through with a further 3 ml MeCN/0.1% TFA
  6. customSolvent was removed by blowdown under a stream of nitrogen
  7. dissolutionThe residue was dissolved in MeOH (0.51)
  8. washthen eluted with 2M ammonia/MeOH
  9. customevaporated to dryness
  10. customThe sample was purified by Mass Directed AutoPrep (Method C)

Sources & evidence

ORD record
ord-32355e155b92499f906cc13497886f0f
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658635B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes