1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 3-(4-Chlorothiazol-2-yl)benzaldehyde

HRID 594290Notes

Reaction equation

HRID 594290 reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([Cl:7])[N:6]=1.[CH:8]([C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1)=[O:9].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:7][C:5]1[N:6]=[C:2]([C:14]2[CH:15]=[C:10]([CH:11]=[CH:12][CH:13]=2)[CH:8]=[O:9])[S:3][CH:4]=1

Participants

6

Reactant 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27343563-Formylphenylboronic acidHCID 123331552,4-Dichlorothiazole

Product 1

HCID 866956183-(4-Chlorothiazol-2-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of commercially available 2,4-dichlorothiazole (800 mg; 5.19 mmol), (3-formylphenyl)boronic acid (833 mg; 5.56 mmol), potassium phosphate tribasic K3PO4 (3.308 g; 15.60 mmol), Xantphos (75 mg; 0.13 mmol), and Pd(OAc)2 (29 mg; 0.13 mmol) in anh. THF (26 ml) was heated to 60° C., under nitrogen, for 3 h. After cooling to rt, the mixture was filtered over celite, and the separated solids were washed with DCM. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 3-(4-chlorothiazol-2-yl)benzaldehyde as a colorless solid. LC-MS (conditions A): tR=0.77 min.; [M+H]+: 224.03 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe mixture was filtered over celite
  3. washthe separated solids were washed with DCM
  4. concentrationConcentration to dryness
  5. customunder reduced pressure, and subsequent purification by FC (DCM)

Sources & evidence

ORD record
ord-889b7ac418b641c995f32f7a0000ce3c
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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