Sodium Carbonate → HCID 86696582、化合物

HRID 1478352ノート

反応式

HRID 1478352 の反応式
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]2=[O:21].[OH:22][C:23]1[CH:28]=[CH:27][C:26](B(O)OC)=[CH:25][CH:24]=1.[C:33]([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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>[OH:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([C:11]=2[CH3:12])=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]3=[O:21])=[C:25]([CH3:33])[CH:24]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 12071709ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylateHCID 66980321HCID 66980321、化合物

生成物 1

HCID 86696582HCID 86696582、化合物収率 40%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (120 mg, 0.400 mmol), 4-hydroxy-methyl-phenyl boronic acid (73 mg, 0.48 mmol), (Ph3P)2PdCl2 (28 mg, 0.040 mmol), and Na2CO3 (190 mg in 0.8 mL of water, 1.80 mmol) in THF (5 mL) was degassed 3 times under N2 and heated to 80° C. overnight. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (2×20 mL). The organic phase was separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 1:3 to pure ethyl acetate) to afford the title compound as a yellow solid (60 mg, 40%).

後処理

  1. customwas degassed 3 times under N2
  2. additionThe reaction mixture was diluted with ethyl acetate (50 mL)
  3. washwashed with water (2×20 mL)
  4. customThe organic phase was separated
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica column chromatography (hexane:ethyl acetate, 1:3 to pure ethyl acetate)

出典と根拠

ORDレコード
ord-26b9688144ed404cbbd9e809d23bd954
出典データセット
uspto-grants-2016_08
特許番号
US09403818B2

反応ノート

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