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

HRID 1771453Notes

Reaction equation

HRID 1771453 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3c534e60dcc64abb98b11ca9c1b020cb
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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