Sodium t-butoxide → HCID 178506000, compound

HRID 707322Notes

Reaction equation

HRID 707322 reaction equation
Cl[C:2]1[C:7]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[CH:6][C:5]([F:12])=[CH:4][N:3]=1.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH:22][C@H:23]1[CH2:26][C@H:25]([NH2:27])[CH2:24]1.CC(C)([O-])C.[Na+]>[Pd+2]>[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH:22][C@H:23]1[CH2:24][C@H:25]([NH:27][C:2]2[C:7]([NH:8][CH:9]3[CH2:11][CH2:10]3)=[CH:6][C:5]([F:12])=[CH:4][N:3]=2)[CH2:26]1

Participants

5

Reactant 3

HCID 23676156Sodium t-butoxideHCID 86694126HCID 86694126, compound2×HCID 178511738HCID 178511738, compound2×

Product 1

HCID 178506000HCID 178506000, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)Catalyst

Conditions

Temperature
80 °C

Procedure

2-Chloro-N-cyclopropyl-5-fluoropyridin-3-amine (intermediate 39, 0.230 g, 1.232 mmol), trans-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine (intermediate 11, 0.270 g, 1.232 mmol), chloro(2-dicyclohexylphosphino-3,6-dimethoxy-2′-4′-6′-triisopropyl-1,1′-biphenyl) 2-(2-aminoethyl)phenyl)palladium(II) (0.049 g, 0.062 mmol), and sodium t-butoxide (0.296 g, 3.08 mmol) were sealed in a microwave vial under argon. Dry, sparged dioxane (1 mL) was added and the reaction heated at 80° C. After 45 minutes the vial was opened and the crude and dry loaded on silica gel. Purification using silica chromatography (hexane to ethyl acetate gradient) gave N2-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-N3-cyclopropyl-5-fluoropyridine-2,3-diamine (0.304 g, 0.824 mmol, 66.8% yield).

Workup

  1. customDry
  2. customsparged dioxane (1 mL)
  3. additionwas added
  4. customthe crude and dry
  5. customPurification

Sources & evidence

ORD record
ord-31ace7519cc04a058ea485a71623f7c2
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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