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Sodium Carbonate → 4-(2-Amino-5-chloropyridin-3-yl)phenol

HRID 1747922
Notes
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Reaction equation

HRID 1747922 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].Br[C:25]1[C:26]([NH2:32])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=1>COCCOC.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>[NH2:32][C:26]1[C:25]([C:18]2[CH:17]=[CH:16][C:15]([OH:14])=[CH:20][CH:19]=2)=[CH:30][C:29]([Cl:31])=[CH:28][N:27]=1.[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:25]2[C:26]([NH2:32])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=2)=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27639713-Bromo-5-chloropyridin-2-amineHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 2

HCID 667480044-(2-Amino-5-chloropyridin-3-yl)phenolHCID 667485503-(4-{[Tert-butyl(dimethyl)silyl]oxy}phenyl)-5-chloropyridin-2-amine

Reagents, catalysts & solvents

3
HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium carbonate (4.09 g), tetrakis(triphenylphosphine)palladium(0) (0.668 g), 4-(tert-butyldimethylsilyloxy)phenylboronic acid (6.32 g) and 3-bromo-5-chloropyridin-2-amine (4.00 g) in DME (100 mL) and water (20 mL) was stirred at 80° C. overnight. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 4-(2-amino-5-chloropyridin-3-yl)phenol (3.05 g) as a pale yellow solid and 3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-chloropyridin-2-amine (1.55 g) as a yellow solid.

Workup

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-87c540d1a82745fa834ebb951151d1f8
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150591B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes