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

HRID 594290노트

반응식

HRID 594290 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-889b7ac418b641c995f32f7a0000ce3c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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