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

HRID 1771453노트

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HRID 1771453 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c534e60dcc64abb98b11ca9c1b020cb
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249132B2

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