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

HRID 594290ノート

反応式

HRID 594290 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-889b7ac418b641c995f32f7a0000ce3c
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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