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2-Thiazolamine, 5-bromo- → 5-[1-Methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole-2-ylamine

HRID 1524243
Notes
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Reaction equation

HRID 1524243 reaction equation
[CH3:1][N:2]1[C:6](B(O)O)=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[NH2:14][C:15]1[S:16][C:17](Br)=[CH:18][N:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:1][N:2]1[C:6]([C:17]2[S:16][C:15]([NH2:14])=[N:19][CH:18]=2)=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 436002-Thiazolamine, 5-bromo-HCID 62657Potassium Phosphate, TribasicHCID 120567131-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acid

Product 1

HCID 866626835-[1-Methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole-2-ylamineYield 1.9%

Reagents, catalysts & solvents 4

HCID 11714597
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
Catalyst
HCID 962WaterSolvent
HCID 6342AcetonitrileSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)boronic acid (290 mg, 1.5 mmol), 2-amino-5-bromothiazole (1 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (A-Phos) (53 mg) and K3PO4 (212 mg, 1 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 70° C. for 1 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. Prep HPLC purification furnished 4.6 mg 5-[1-methyl-3-(trifluoromethyl)pyrazol-5-yl]-1,3-thiazole-2-ylamine (63) as light yellow solid (yield 1.9%; purity>95%).

Workup

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customPrep HPLC purification

Sources & evidence

ORD record
ord-bd185c6d38b746c3a0f2d3eadb7a87c0
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09079891B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes