Ethyl Acetate → Ethyl 6-bromo-8-phenylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1958474ノート

反応式

HRID 1958474 の反応式
Br.[Br:2][C:3]1[CH:4]=[C:5](Br)[C:6]2[N:7]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:8]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:2][C:3]1[CH:4]=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:6]2[N:7]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:8]=1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 67007442Ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide

生成物 1

HCID 58208011Ethyl 6-bromo-8-phenylimidazo[1,2-a]pyridine-2-carboxylate収率 58%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A solution of ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide (0.5 g, 1.2 mmol) and phenylboronic acid (0.15 g, 1.2 mmol) in toluene (10 mL) and ethanol (2 mL) was bubbled nitrogen for 20 mins. The mixture was then treated with Pd(PPh3)4 (30 mg, 0.026 mmol) and K3PO4 (2 M, 1 mL, 2 mmol) and heated at 80° C. overnight. The reaction was cooled, poured into ethyl acetate (200 mL), washed with brine, separated, and concentrated. The residue was purified by column chromatography on silica gel using ethyl acetate in hexanes (10%) as eluent. The product containing fractions were concentrated to give 0.23 g (58% yield) of ethyl 6-bromo-8-phenylimidazo[1,2-a]pyridine-2-carboxylate as a white solid. LCMS (Conditions C): 3.41 min (RT); (M+H)+=347.24 (100%), 345.24 (100%). 1H NMR, 400 MHz, CDCl3: δ 8.27 (d, J=1.6 Hz, 1 H), 8.19 (s, 1 H), 8.02 (m, 2H), 7.52-7.41 (m, 4 H), 4.45 (q, J=7.1 Hz, 2 H), 1.42 (t, J=7.0 Hz, 3 H).

後処理

  1. temperatureThe reaction was cooled
  2. washwashed with brine
  3. customseparated
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel
  6. additionThe product containing fractions
  7. concentrationwere concentrated

出典と根拠

ORDレコード
ord-81e5a43598aa46bb8284a4c1f326a778
出典データセット
uspto-grants-2013_04
特許番号
US08410128B2

反応ノート

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