Sodium Carbonate → Methyl 6-(6-hydroxynaphthalen-2-yl)nicotinate

HRID 1771453ノート

反応式

HRID 1771453 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](B(O)O)[CH:6]=[CH:5]2.Br[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1)[CH:6]=[CH:5]2

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 4349738(6-Hydroxynaphthalen-2-yl)boronic acidHCID 13349623Methyl 6-bromopyridine-3-carboxylate

生成物 1

HCID 136331263Methyl 6-(6-hydroxynaphthalen-2-yl)nicotinate

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

A mixture of 6-hydroxynaphthalen-2-ylboronic acid (250 mg, 1.33 mmol), methyl 6-bromonicotinate (260 mg, 1.21 mmol), Pd(dppf)Cl2 (90 mg, 0.12 mmol) and sodium carbonate (205 mg, 2.41 mmol) in DME/water (3 mL/1 mL) was heated to 120° C. by microwave for 1 h. Then the mixture was partitioned with water (10 mL) and EA (20 mL). The precipitate was filtered off. The organic phase was separated, washed with brine (15 mL), dried over Na2SO4 and concentrated to afford product (crude, 380 mg) as a brown oil.

後処理

  1. customThen the mixture was partitioned with water (10 mL) and EA (20 mL)
  2. filtrationThe precipitate was filtered off
  3. customThe organic phase was separated
  4. washwashed with brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford product (crude, 380 mg) as a brown oil

出典と根拠

ORDレコード
ord-3c534e60dcc64abb98b11ca9c1b020cb
出典データセット
uspto-grants-2016_02
特許番号
US09249132B2

反応ノート

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