1,2-Dimethoxyethane → HCID 68312478、化合物

HRID 1472894ノート

反応式

HRID 1472894 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[N:20]=[C:19]([CH3:21])[C:18]([CH3:22])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].COCCOC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O.C(O)C.O>[CH3:22][C:18]1[CH:17]=[CH:16][C:15]([C:6]2[CH:7]=[N:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[N:20][C:19]=1[CH3:21]

参加物

9

反応物 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 251342782-(Trifluoromethyl)pyridine-5-boronic AcidHCID 457912776-Bromo-2,3-dimethylpyridine

生成物 1

HCID 68312478HCID 68312478、化合物収率 294.4%

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A 20 mL microwave vial was charged with 6-(trifluoromethyl)pyridin-3-ylboronic acid (564 mg, 2.96 mmol), 6-bromo-2,3-dimethylpyridine (500 mg, 2.69 mmol), bis(triphenylphosphine)palladium(II) chloride (94 mg, 0.134 mmol), and K2CO3 (743 mg, 5.37 mmol), followed by the addition of DME (9.0 mL), water (3.86 mL) and ethanol (2.57 mL). The reaction mixture was heated in a microwave at 120° C. for 10 minutes. To the reaction mixture was added 200 mL EtOAc, and washed with 200 mL water and 200 mL brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on a Grace Reveleris 40 g column, eluted with 0-40% EtOAc in Hexanes (25 mL/min) to provide the title compound (1.997 g, 7.92 mmol, 98% yield) as a white solid. MS (ESI+) m/z 253.2 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 9.40 (d, J=1.9, 1H), 8.68 (dd, J=8.3, 1.7, 1H), 8.00 (d, J=8.3, 1H), 7.92 (d, J=7.9, 1H), 7.71 (d, J=7.9, 1H), 2.54 (s, 3H), 2.33 (s, 3H).

後処理

  1. washwashed with 200 mL water and 200 mL brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a Grace Reveleris 40 g column
  6. washeluted with 0-40% EtOAc in Hexanes (25 mL/min)

出典と根拠

ORDレコード
ord-e5a557b3b8c84c7bb012058558861ce2
出典データセット
uspto-grants-2015_04
特許番号
US09012651B2

反応ノート

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