HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Phosphate, Tribasic → 5-(3,3,6-Trimethyl-2,3-dihydrobenzo[3,4-b]furan-5-yl)-2-pyridylamine

HRID 874661
Notes
Print preview

Reaction equation

HRID 874661 reaction equation
Br[C:2]1[C:12]([CH3:13])=[CH:11][C:5]2[O:6][CH2:7][C:8]([CH3:10])([CH3:9])[C:4]=2[CH:3]=1.FC1(F)OC2C=C(C)C(C3N=C[C:27]([NH:30][C:31](=O)[C:32]4[CH:37]=[CH:36]C=CC=4F)=[N:28]C=3)=CC=2O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O>[CH3:9][C:8]1([CH3:10])[CH2:7][O:6][C:5]2[CH:11]=[C:12]([CH3:13])[C:2]([C:32]3[CH:37]=[CH:36][C:27]([NH2:28])=[N:30][CH:31]=3)=[CH:3][C:4]1=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 186992015-Bromo-3,3,6-trimethyl-2,3-dihydro-benzofuranHCID 58486754N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamide

Product 1

HCID 584871355-(3,3,6-Trimethyl-2,3-dihydrobenzo[3,4-b]furan-5-yl)-2-pyridylamineYield 90.8%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-bromo-3,3,6-trimethyl-2,3-dihydrobenzo[b]furan (171) (241 mg, 1 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (330 mg, 1.5 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (106 mg), and K3PO4 (636 mg) in 3 ml ACN, 3 ml dioxane, 1.5 ml H2O was bubbled with argon before heated at 85° C. for 2.5 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 silica gel column purification to give 231 mg 5-(3,3,6-trimethyl-2,3-dihydrobenzo[3,4-b]furan-5-yl)-2-pyridylamine (172) (yield: 90.8%, purity>95%) as thick yellow oil.

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. customsubjected silica gel column purification

Sources & evidence

ORD record
ord-deab828ee17a4e8fb9684fbe20e05e74
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08980629B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes