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Ammonium Chloride → HCID 86700075, compound

HRID 1428122
Notes
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Reaction equation

HRID 1428122 reaction equation
I[C:2]1[C:3]([NH2:10])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CC1(C)C(C)(C)OB([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)O1.[F-].[Cs+].[Cl-].[NH4+]>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[NH2:23][C:22]1[CH:24]=[CH:25][C:19]([C:2]2[C:3]([NH2:10])=[N:4][CH:5]=[CH:6][C:7]=2[O:8][CH3:9])=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 25953Cesium fluorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 242292063-Iodo-4-methoxypyridin-2-amine

Product 1

HCID 86700075HCID 86700075, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Iodo-4-methoxypyridin-2-amine (350 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (322 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane adduct (81 mg) and cesium fluoride (580 mg) were suspended in methanol (5.0 ml), and the suspension was heated under reflux at 80° C. for 19 hours. After leaving to cool, a saturated aqueous ammonium chloride solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate:dichloromethane:methanol=5:5:1 (v/v)] to give 245 mg of the title compound as a solid.

Workup

  1. temperaturethe suspension was heated
  2. customAfter leaving
  3. temperatureto cool
  4. extractionthe organic layer was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [ethyl acetate:dichloromethane:methanol=5:5:1 (v/v)]

Sources & evidence

ORD record
ord-8c244f861e66497b9fc123d87b1078ba
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933103B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes