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Ethanol → 4-Chloro-2-(pyridin-3-yl)thiazole

HRID 533344
Notes
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Reaction equation

HRID 533344 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Cl[C:11]1[S:12][CH:13]=[C:14]([Cl:16])[N:15]=1.C(O)C.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.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:16][C:14]1[N:15]=[C:11]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[S:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 123331552,4-Dichlorothiazole

Product 1

HCID 595806044-Chloro-2-(pyridin-3-yl)thiazoleYield 78%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of pyridin-3-ylboronic acid (3.87 g, 31.5 mmol) in toluene (120 mL) was added 2,4-dichlorothiazole (4.62 g, 30 mmol) followed by ethanol (60 mL) and a 2.0 M solution of K2CO3 (30.0 mL, 60.0 mmol). The solution was degassed by applying vacuum and then purging with nitrogen (3 times). To the reaction mixture was added tetrakis(triphenylphosphine)palladium (0) (1.733 g, 1.500 mmol) and the flask was heated at 95° C. under nitrogen for 16 hours. The aqueous layer was removed and the organic layer was concentrated. The crude product was purified via silica gel chromatography (0-100% ethyl acetate/hexanes) to afford the title compound as a brown solid (4.6 g, 74%): mp 84-86° C.; IR (KBr) 3092 cm−1; 1H NMR (400 MHz, CDCl3) δ 9.16-9.13 (m, 1H), 8.69 (dd, J=4.8, 1.6 Hz, 1H), 8.23 (ddd, J=8.0, 2.2, 1.7 Hz, 1H), 7.40 (ddd, J=8.0, 4.8, 0.8 Hz, 1H), 7.16 (s, 1H).

Workup

  1. customThe solution was degassed
  2. custompurging with nitrogen (3 times)
  3. customThe aqueous layer was removed
  4. concentrationthe organic layer was concentrated
  5. customThe crude product was purified via silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-19173f8c915c48c89b27a11335910ef9
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853246B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes