Potassium Phosphate, Tribasic → HCID 58486925, compound

HRID 1036124Notes

Reaction equation

HRID 1036124 reaction equation
Br[C:2]1[C:3]([Cl:11])=[CH:4][C:5]2[CH2:9][CH2:8][O:7][C:6]=2[CH:10]=1.FC1(F)OC2C=C(C)C([C:22]3[CH:23]=[CH:24][C:25]([NH:28]C(=O)C4C=CC=CC=4F)=[N:26][CH:27]=3)=CC=2O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O.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>[Cl:11][C:3]1[C:2]([C:22]2[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=2)=[CH:10][C:6]2[O:7][CH2:8][CH2:9][C:5]=2[CH:4]=1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 584868281345120-17-3HCID 58487315HCID 58487315, compound

Product 1

HCID 58486925HCID 58486925, compoundYield 75.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-bromo-5-chloro-2,3-dihydrobenzo[b]furan (18) (233 mg, purity ca 60%, ca 0.6 mmol), 2-aminopyridine-5-boronic acid pinacol ester (6) (220 mg, 1 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (36 mg, 10% mol), Pd(PPh3)4 (58 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 85° C. for 4 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected to prep HPLC purification to give 5-(5-chloro-2,3-dihydrobenzo[3,4-b]furan-6-yl)-2-pyridylamine (19) (111.8 mg, yield: 75.5%, purity>95%) as yellow solid.

Workup

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated
  6. customHPLC purification

Sources & evidence

ORD record
ord-cb14959e32f8499d90c546c44ea36b0b
Source dataset
uspto-grants-2013_10
Patent number
US08546403B2

Reaction notes

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