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Toluene → HCID 86676502, compound

HRID 1854625
Notes
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Reaction equation

HRID 1854625 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][C:19]([Sn](CCCC)(CCCC)CCCC)=[CH:20][N:21]=2)=[CH:13][CH:12]=1.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.O>[Br:8][C:4]1[N:3]=[C:2]([C:19]2[S:18][C:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=3)=[N:21][CH:20]=2)[CH:7]=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1140TolueneHCID 122742,6-DibromopyridineHCID 67324907HCID 67324907, compound

Product 1

HCID 86676502HCID 86676502, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962
Water
Solvent

Procedure

A sealed tube was charged with 2,6-dibromopyridine (474 mg, 2.00 mmol), 2-(4-methoxyphenyl)-5-(tributylstannyl)thiazole (920 mg, 2.00 mmol), Pd(PPh3)4 (231 mg, 0.20 mmol), and anhydrous and degazed toluene (9 ml) and heated to 120° C. with stirring for 24 hours. The cooled reaction mixture was treated with water and extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure before purification by dry flash chromatography over SiO2 eluting with EtOAc/cyclohexane 20/80 to give 5-(6-bromopyridin-2-yl)-2-(4-methoxyphenyl)thiazole (410 mg, 59%). 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.06 (d, J=7.2 Hz, 1H), 7.96 (d, J=8.3 Hz, 2H), 7.82 (t, J=7.8 Hz, 1H), 7.57 (d, J=7.3 Hz, 1H), 7.07 (d, J=8.5 Hz, 2H), 3.83 (s, 3H).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure before purification
  6. dry with materialby dry flash chromatography over SiO2 eluting with EtOAc/cyclohexane 20/80

Sources & evidence

ORD record
ord-c6d06056c8e34d3b9a92db861d0aed96
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes