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Methanol → Methyl 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate

HRID 1502457
ノート
印刷プレビュー

反応式

HRID 1502457 の反応式
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:4][N:3]=1.F[B-](F)(F)F.F[B-](F)(F)F.C1(P(C2CCCCC2)CCCP(C2CCCCC2)C2CCCCC2)CCCCC1.[C:57](=[O:60])([O-])[O-:58].[K+].[K+].[CH3:63]O>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:6]1[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:4][N:3]=[C:2]([C:57]([O:58][CH3:63])=[O:60])[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 71317487Phosphine, 1,1'-(1,3-propanediyl)bis[1,1-dicyclohexyl-, tetrafluoroborate(1-) (1:2)HCID 722214742-Chloro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridine

生成物 1

HCID 67977255Methyl 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate収率 64.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-chloro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (500 mg, 1.97 mmol), 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) (125 mg, 0.20 mmol), palladium(II) acetate (22 mg, 0.10 mmol), potassium carbonate (413 mg, 2.96 mmol), and methanol (1.20 mL, 29.59 mmol) in DMF (6 mL) was evacuated and then filled with nitrogen (3×), and then evacuated and filled with carbon monoxide (2×). The reaction mixture was then heated at 100° C. for 2 hours under a balloon of carbon monoxide. The cooled reaction was diluted with ethyl acetate (10 mL), filtered over Celite, and concentrated in vacuo to provide a dark red residue that was filtered through a silica plug, eluting with ethyl acetate (60 mL). The pale yellow eluent was concentrated in vacuo to afford the title compound as a yellow oil (350 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.91 (s, 1H), 4.00 (s, 3H), 2.59 (s, 3H), 1.36 (s, 12H).

後処理

  1. customwas evacuated
  2. additionfilled with nitrogen (3×)
  3. customevacuated
  4. additionfilled with carbon monoxide (2×)
  5. customThe cooled reaction
  6. filtrationfiltered over Celite
  7. concentrationconcentrated in vacuo
  8. customto provide a dark red residue that
  9. filtrationwas filtered through a silica plug
  10. washeluting with ethyl acetate (60 mL)
  11. concentrationThe pale yellow eluent was concentrated in vacuo

出典と根拠

ORDレコード
ord-a4df4c98b301411da064d73cd079cb9c
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206175B2

反応ノート

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